Fused heterocyclic compound

ABSTRACT

There is provided a compound having an excellent controlling effect on pests represented by the formula (1): 
     
       
         
         
             
             
         
       
     
     wherein, A 1  represents —NR 7 —, etc., A 2  represents a nitrogen atom, etc., A 3  represents a nitrogen atom, etc., R 1  represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X, etc., R 2 , R 3  and R 4  are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, etc., R 5  and R 6  are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X, etc., R 7  represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group W, etc., n represents 0, 1 or 2, or an N-oxide thereof.

TECHNICAL FIELD

The present application is filed claiming the priority of the JapanesePatent Application Nos. 2011-170833, 2012-079323 and 2012-122837, theentire contents of which are herein incorporated by reference.

The present invention relates to a fused heterocyclic, compound and theuse thereof for pest control.

BACKGROUND ART

For controlling pests, various compounds have been developed and usedpractically.

Further, some fused heterocyclic compounds are known (see, PatentLiterature 1).

CITATION LIST Patent Literature

Patent Literature 1: JP-A-2004-34438

SUMMARY OF INVENTION Technical Problem

An object of the present invention is to provide a novel compound havingan excellent controlling effect on pests and a method for controllingpests with said compound.

Solution to Problem

The inventors of the present invention have intensively studied, and asa result, they have found that a fused heterocyclic compound representedby the following formula (1) has an excellent controlling effect onpests. Thus, the present invention has been completed.

The present invention includes the followings:

[1] A fused heterocyclic compound represented by the formula (1):

whereinA¹ represents —NR⁷—, an oxygen atom or a sulfur atom,A² represents a nitrogen atom or ═CR⁸—,A³ represents a nitrogen atom or ═CR⁹—,R¹ represents a C1-C6 chain hydrocarbon group optionally substituted byone or more atoms or groups selected from Group X or a C3-C6 alicyclichydrocarbon group optionally substituted by one or more atoms or groupsselected from Group Y,R², R³ and R⁴ are the same or different and each represents a C1-C6chain hydrocarbon group optionally substituted by one or more atoms orgroups selected from Group X, a phenyl group optionally substituted byone or more atoms or groups selected from Group Z, a 5- or 6-memberedheterocyclic group optionally substituted by one or more atoms or groupsselected from Group Z, —OR¹⁰, —S(O)_(m)R¹⁰, —S(O)₂NR¹⁰R¹¹, —NR¹⁰R¹¹,—NR¹⁰CO₂R¹¹, —CO₂R¹⁰, —C(O)R¹⁰, —NR¹⁰R¹¹, —SF₅, a cyano group; a nitrogroup, a halogen atom or a hydrogen atom,R⁵ and R⁶ are the same or different and each represents a C1-C6 chainhydrocarbon group optionally substituted by one or more atoms or groupsselected from Group X, a phenyl group optionally substituted by one ormore atoms or groups selected from Group Z, a 5- or 6-memberedheterocyclic group optionally substituted by one or more atoms or groupsselected from Group Z, —OR¹⁰, —S(O)_(m)R¹⁰, —S(O)₂NR¹⁰R¹¹, NR¹⁰R¹¹,—NR¹⁰CO₂R¹¹, —NR¹⁰C(O)R¹¹, —CO₂R¹⁰, —C(O)R¹⁰, C(O)NR¹⁰R¹¹, —SF₅, a cyanogroup, a nitro group, a halogen atom or a hydrogen atom (wherein R⁵ andR⁶ do not represents a hydrogen atom at the same time),R⁷ represents a C1-C6 chain hydrocarbon group optionally substituted byone or more atoms or groups selected from Group W, a C1-C6 chainhydrocarbon group substituted by one phenyl group (wherein the phenylgroup is optionally substituted by one or more atoms or groups selectedfrom Group Z), a C1-C6 chain hydrocarbon group substituted by one 5- or6-membered heterocyclic group (wherein the 5- or 6-membered heterocyclicgroup is optionally substituted by one or more atoms or groups selectedfrom Group Z), —CO₂R¹⁰, —C(O)R¹⁰, a C3-C6 alicyclic hydrocarbon groupoptionally substituted by one or more atoms or groups selected fromGroup Y or a hydrogen atom,R⁸ and R⁹ are the same or different and each represents a C1-C6 chainhydrocarbon group optionally substituted by one or more halogen atoms,—OR¹⁰, —S(O)R¹⁰, —NR¹⁰R¹¹, —CO₂R¹⁰, —C(O)R¹⁰, a cyano group, a nitrogroup, a halogen atom or a hydrogen atom,R¹⁰ and R¹¹ are the same or different and each represents a C1-C6 chainhydrocarbon group optionally substituted by one or more atoms or groupsselected from Group X, a phenyl group optionally substituted by one ormore atoms or groups selected from Group Z or a hydrogen atom,each m independently represents 0, 1 or 2, andn represents 0, 1 or 2,wherein the —S(O)_(m)R¹⁰, R¹⁰ does not a hydrogen atom when m is 1 or 2,Group X: the group consisting of a C1-C6 alkoxy group optionallysubstituted by one or more halogen atoms, a C2-C6 alkenyloxy groupoptionally substituted by one or more halogen atoms, a C2-C6 alkynyloxygroup optionally substituted by one or more halogen atoms, a C1-C6alkylsulfanyl group optionally substituted by one or more halogen atoms,a C1-C6 alkylsulfinyl group optionally substituted by one or morehalogen atoms, a C1-C6 alkylsulfonyl group optionally substituted by oneor more halogen atoms, a C2-C6 alkylcarbonyl group optionallysubstituted by one or more halogen atoms, a C2-C6 alkoxycarbonyl, groupoptionally substituted by one or more halogen atoms, a C3-C6 cycloalkylgroup optionally substituted by one or more halogen atoms or one or moren-alkyl groups, a cyano group, a hydroxy group and a halogen atom,Group Y: the group consisting of a C1-C6 chain hydrocarbon groupoptionally substituted by one or more halogen atoms, a C1-C6 alkoxygroup optionally substituted by one or more halogen atoms, a C2-C6alkenyloxy group optionally substituted by one or more halogen atoms, aC2-C6 alkynyloxy group optionally substituted by one or more halogenatoms and a halogen atom,Group Z: the group consisting of a C1-C6 chain hydrocarbon groupoptionally substituted by one or more halogen atoms, a C1-C6 alkoxygroup optionally substituted by one or more halogen atoms, a C1-C6alkylsulfanyl group optionally substituted by one or more halogen atoms,a C1-C6 alkylsulfinyl group optionally substituted by one or morehalogen atoms, a C1-C6 alkylsulfonyl group optionally substituted by oneor more halogen atoms, a C2-C6 alkylcarbonyl group optionallysubstituted by one or more halogen atoms, a C2-C6 alkoxycarbonyl groupoptionally substituted by one or more halogen atoms, a C1-C6 alkylaminogroup optionally substituted by one or more halogen atoms, a C2-C8dialkylamino group optionally substituted by one or more halogen atoms,a halogen atom, a cyano group and a nitro group,Group W: the group consisting of a C1-C6 alkoxy group optionallysubstituted by one or more halogen atoms, a C2-C6 alkenyloxy groupoptionally substituted by one or more halogen atoms, a C2-C6 alkynyloxygroup optionally substituted by one or more halogen atoms, a C1-C6alkylsulfanyl group optionally substituted by one or more halogen atoms,a C2-C6 alkylcarbonyl group optionally substituted by one or morehalogen atoms, a C2-C6 alkoxycarbonyl group optionally substituted byone or more halogen atoms, a C3-C6 cycloalkyl group optionallysubstituted by one or more halogen atoms, a C1-C6 alkylsulfinyl groupoptionally substituted by one or more halogen atoms, a C1-C6alkylsulfonyl group optionally substituted by one or more halogen atoms,hydroxy group, a halogen atom and a cyano group,or an N-oxide thereof (hereinafter referred to as “the presentcompound”).[2] The compound according to the above [1], whereinA¹ is —NR⁷—, an oxygen atom or a sulfur atom,A² is a nitrogen atom or ═CR⁸—,A³ is a nitrogen atom or ═CR⁹—,R¹ is a C1-C6 chain hydrocarbon group optionally substituted by one ormore atoms or groups selected from Group X,R², R³ and R⁴ are the same or different and each represents a C1-C6chain hydrocarbon group optionally substituted by one or more atoms orgroups selected from Group X, a phenyl group optionally substituted byone or more atoms or groups selected from Group Z, a 5- or 6-memberedheterocyclic group optionally substituted by one or more atoms or groupsselected from Group Z, —OR¹⁰, —S(O)_(m)R¹⁰, —SF₅, a cyano group, a nitrogroup, a halogen atom or a hydrogen atom,R⁵ and R⁶ are the same or different and each represents a C1-C6 chainhydrocarbon group optionally substituted by one or more atoms or groupsselected from Group X, —OR¹⁰, S(O)_(m)R¹⁰, —SF₅, a halogen atom or ahydrogen atom,R⁷ is a C1-C6 chain hydrocarbon group optionally substituted by one ormore atoms or groups selected from Group W, a C1-C6 chain hydrocarbongroup substituted by one phenyl group (wherein the phenyl group isoptionally substituted by one or more atoms or groups selected fromGroup Z), a C1-C6 chain hydrocarbon group substituted by one 5- or6-membered heterocyclic group (wherein the 5- or 6-membered heterocyclicgroup is optionally substituted by one or more atoms or groups selectedfrom Group Z), or a hydrogen atom,R⁸ is a C1-C6 chain hydrocarbon group optionally substituted by one ormore halogen atoms, —OR¹⁰, —S(O)_(m)R¹⁰, a halogen atom or a hydrogenatom, andR⁹ is a C1-C6 chain hydrocarbon group optionally substituted by one ormore halogen atoms, —OR¹⁰, —S(O)_(m)R¹⁰, a halogen atom or a hydrogenatom.[3] The compound according to the above. [1], whereinA¹ is —NR⁷—, an oxygen atom or a sulfur atom,A² is a nitrogen atom or ═CR⁸—,A³ is a nitrogen atom or ═CR⁹—,R¹ is a C1-C6 alkyl group optionally substituted by one or more atoms orgroups selected from the group consisting of a halogen atom andcyclopropyl group (wherein the cyclopropyl group is optionallysubstituted by one or more halogen atoms or one or more C1-C3 alkylgroup), a C2-C6 alkenyl group optionally substituted by one or morehalogen atoms or a C2-C6 alkynyl group optionally substituted by one ormore halogen atoms,R² and R⁴ are the same or different each other and each represents ahalogen atom or a hydrogen atom,R³ is a C1-C6 alkyl group optionally substituted by one or more halogenatoms, a C2-C6 alkenyl group optionally substituted by one or morehalogen atoms, a C2-C6 alkynyl group optionally substituted by one ormore halogen atoms, 5- or 6-membered aromatic heterocyclic group(wherein the 5- or 6-membered aromatic heterocyclic group is optionallysubstituted by one or more atoms or groups selected from the groupconsisting of a halogen atom, a C1-C3 alkyl group optionally substitutedby one or more halogen atoms, and a C1-C3 alkoxy group optionallysubstituted by one or more halogen atoms), —OR¹⁰, —S(O)_(m)R¹⁰, a cyanogroup, a nitro group, a halogen atom or a hydrogen atom,R⁵ is a C1-C6 alkyl group optionally substituted by one or more halogenatoms, —OR¹⁰, —S(O)_(m)R¹⁰, —SF₅ or a halogen atom,R⁶ is a C1-C6 alkyl group optionally substituted by one or more halogenatoms, —OR¹⁰, —S(O)_(m)R¹⁰, a halogen atom or a hydrogen atom,R¹⁰ is a C1-C6 alkyl group optionally substituted by one or more halogenatoms,R⁷ is a C1-C6 alkyl group optionally substituted by one or more halogenatoms, a C3-C6 alkenyl group optionally substituted by one or morehalogen atoms, a, C3-C6 alkynyl group optionally substituted by one ormore halogen atoms, a C1-C6 alkyl group substituted by one 5- or6-membered aromatic heterocyclic group (wherein the 5- or 6-memberedaromatic heterocyclic group is optionally substituted by one or moreatoms or groups selected from the group consisting of a halogen atom, aC1-C3 alkyl group optionally substituted by one or more halogen atoms,and a C1-C3 alkoxy group optionally substituted by one or more halogenatoms), a hydrogen atom or a C2-C6 alkoxyalkyl group optionallysubstituted by one or more halogen atoms,R⁸ is a C1-C6 alkyl group optionally substituted by one or more halogenatoms, —OR¹⁰, —S(O)_(m)R¹⁰, a halogen atom or a hydrogen atom, andR⁹ is a C1-C6 alkyl group optionally substituted by one or more halogenatoms, —OR¹⁰, —S(O)_(m)R¹⁰, a halogen atom or a hydrogen atom.[4] The compound according to any one of the above [1][3], wherein A¹ is —NR⁷—.[5] The compound according to any one of the above [1] to [3], whereinA¹ is an oxygen atom.[6] The compound according to any one of the above [1] to [3], whereinA¹ is a sulfur atom.[7] The compound according to any one of the above [1] to [6], whereinA² is ═CR⁸—.[8] The compound according to any one of the above [1] to [6], whereinA² is ═CR⁸—, and A³ is a nitrogen atom.[9] The compound according to any one of the above [1] to [6], whereinA² is ═CR⁸—, and A³ is ═CR⁹—.[10] A compound represented by the formula (1-1):

whereinA^(1a) represents —NR^(7a)—, an oxygen atom or a sulfur atom,A^(3a) represents a nitrogen atom or ═CR^(9a)—,R^(1a) represents a C1-C6 alkyl group optionally substituted by one ormore atoms or groups selected from the group consisting of a halogenatom and a cyclopropyl group (wherein the cyclopropyl group isoptionally substituted by one or more halogen atoms or one or more C1-C3alkyl groups), a C2-C6 alkenyl group optionally substituted by one ormore halogen atoms or a C2-C6 alkynyl group optionally substituted byone or more halogen atoms,R^(2a) and R^(4a) are the same or different and each represents ahalogen atom or a hydrogen atom,R^(3a) represents a C1-C6 alkyl group optionally substituted by one ormore halogen atoms, a C2-C6 alkenyl group optionally substituted by oneor more halogen atoms, a C2-C6 alkynyl group optionally substituted byone or more halogen atoms, 5- or 6-membered aromatic heterocyclic group(wherein the 5- or 6-membered aromatic heterocyclic group is optionallysubstituted by one or more atoms or groups selected from the groupconsisting of a halogen atom, a C1-C3 alkyl group optionally substitutedby one or more halogen atoms, and a C1-C3 alkoxy group optionallysubstituted by one or more halogen atoms), —OR^(20a) (wherein R^(20a)represents a C1-C6 alkyl group optionally substituted by one or morehalogen atoms), —S(O)_(m)R^(21a) (wherein R^(21a) represents a C1-C6alkyl group optionally substituted by one or more halogen atoms, mrepresents 0, 1 or 2), a cyano group, a nitro group, a halogen atom or ahydrogen atom,R^(5a) represents a C1-C6 alkyl group optionally substituted by one ormore halogen atoms, —OR^(22a) (wherein R^(22a) represents a C1-C6 alkylgroup optionally substituted by one or more halogen atoms),—S(O)_(m)R^(23a) (wherein R^(23a) represents a C1-C6 alkyl groupoptionally substituted by one or more halogen atoms, m represents 0, 1or 2), —SF₅ or a halogen atom,R^(7a) represents a C1-C6 alkyl group optionally substituted by one ormore halogen atoms, a C3-C6 alkenyl group optionally substituted by oneor more halogen atoms, a C3-C6 alkynyl group optionally substituted byone or more halogen atoms or a C1-C6 alkyl group substituted by one 5-or 6-membered aromatic heterocyclic group, (wherein the 5- or 6-memberedaromatic heterocyclic group is optionally substituted by one or moreatoms or groups selected from the group consisting of a halogen atom, aC1-C3 alkyl group optionally substituted by one or more halogen atoms,and a C1-C3 alkoxy group optionally substituted by one or more halogenatoms),R^(9a) represents a C1-C6 alkyl group optionally substituted by one ormore halogen atoms, —OR^(24a) (wherein R^(24a) represents a C1-C6 alkylgroup optionally substituted by one or more halogen atoms),—S(O)_(m)R^(25a) (wherein R^(25a) represents a C1-C6 alkyl groupoptionally substituted by one or more halogen atoms, m represents 0, 1or 2), a halogen atom or a hydrogen atom, andn represents 0, 1 or 2,or an N-oxide thereof.[11] The compound according to the above [10], whereinA^(1a) is —NR^(7a)—, an oxygen atom or a sulfur atom,A^(3a) is a nitrogen atom or ═CR^(9a)—,R^(1a) is a C2-C6 alkyl group, a C1-C6 haloalkyl group or C4-C9cyclopropylalkyl group (wherein the cyclopropyl group is optionallysubstituted by one or more halogen atoms or one or more C1-C3 alkylgroups),R^(2a) and R^(4a) both are a hydrogen atom,R^(3a) is a C1-C6 alkyl group optionally substituted by one or morehalogen atoms, a C2-C6 alkenyl group optionally substituted by one ormore halogen atoms, a C2-C6 alkynyl group optionally substituted by oneor more halogen atoms, pyridyl group (wherein the pyridyl group isoptionally substituted by one or more atoms or groups selected from thegroup consisting of a halogen atom, a C1-C3 alkyl group optionallysubstituted by one or more halogen atoms, and a C1-C3 alkoxy groupoptionally substituted by one or more halogen atoms), a pyrimidinylgroup (wherein the pyrimidinyl group is optionally substituted by one ormore atoms or groups selected from the group consisting of halogen atom,a C1-C3 alkyl group optionally substituted by one or more halogen atoms,and a C1-C3 alkoxy group optionally substituted by one or more halogenatoms), —OR^(20a) (wherein R^(20a) is a C1-C6 alkyl group optionallysubstituted by one or more halogen atoms), —S(O)_(m)R^(21a) (whereinR^(21a) is a C1-C6 alkyl group optionally substituted by one or morehalogen atoms, and m is 0, 1 or 2), a halogen atom or a hydrogen atom,R^(5a) is a C1-C6 haloalkyl group, —OR^(22a) (wherein R^(22a) is a C1-C6haloalkyl group), —S(O)_(m)R^(23a) (wherein R^(23a) is a C1-C6 haloalkylgroup, and m is 0, 1 or 2), —SF₅ or a halogen atom, andR^(7a) is a C1-C6 alkyl group optionally substituted by one or morehalogen atoms, a C3-C6 alkenyl group optionally substituted by one ormore halogen atoms, a C3-C6 alkynyl group optionally substituted by oneor more halogen atoms, a C1-C6 alkyl group substituted by one thiazolylgroup (wherein the thiazolyl group is optionally substituted by one ormore atoms or groups selected from the group consisting of a halogenatom, a C1-C3 alkyl group optionally substituted by one or more halogenatoms, and a C1-C3 alkoxy group optionally substituted by one or morehalogen atoms) or a C1-C6 alkyl group substituted by one pyridyl group(wherein the pyridyl group is optionally substituted by one or moreatoms or groups selected from the group consisting of a halogen atom, aC1-C3 alkyl group optionally substituted by one or more halogen atoms,and a C1-C3 alkoxy group optionally substituted by one or more halogenatoms).[12] The compound according to the above [10] or [11], wherein A^(1a) is—NR^(7a)—.[13] The compound according to the above [10] or [11], wherein A^(1a) isan oxygen atom.[14] The compound according to the above [10] or [11], wherein A^(1a) isa sulfur atom.[15] A compound represented by the formula (1-2):

whereinA^(3b) represents a nitrogen atom or ═CR^(9b)— (wherein R^(9b)represents a hydrogen atom or a halogen atom),R^(1b) represents an ethyl group or a cyclopropylmethyl group,R^(7b) represents methyl group or a propargyl group,R^(3b) represents a C1-C6 alkyl group optionally substituted by one ormore halogen atoms, —OR^(20b) (wherein R^(20b) represents a C1-C6 alkylgroup optionally substituted by one or more halogen atoms),—S(O)_(m)R^(21b) (wherein R^(21b) represents a C1-C6 alkyl groupoptionally substituted by one or more halogen atoms, m represents 0, 1or 2), a halogen atom or a hydrogen atom,R^(5b) represents a C1-C6 haloalkyl group, —OR²² (wherein R^(22b)represents a C1-C6 haloalkyl group), —S(O)—R^(23b) (wherein R^(23b)represents a C1-C6 haloalkyl group, m represents 0, 1 or 2), —SF₅ or ahalogen atom, andn represents 0, 1 or 2,or an N-oxide thereof.[16] A compound represented by the formula (1-3):

whereinA^(3b) represents a nitrogen atom or ═CR^(9b)— (wherein R^(9b)represents a hydrogen atom or a halogen atom),R^(1b) represents an ethyl group or a cyclopropylmethyl group,R^(3b) represents a C1-C6 alkyl group optionally substituted by one ormore halogen atoms, —OR^(20b) (wherein R^(20b) represents a C1-C6 alkylgroup optionally substituted by one or more halogen atoms),—S(O)_(m)R^(21b) (wherein R^(21b) represents a C1-C6 alkyl groupoptionally substituted by one or more halogen atoms, m represents 0, 1or 2), a halogen atom or a hydrogen atom,R^(5b) represents a C1-C6 haloalkyl group, —OR^(22b)(wherein R^(22b)represents a C1-C6 haloalkyl group), —S(O)_(m)R^(23b) (wherein R^(23b)represents a C1-C6 haloalkyl group, m represents 0, 1 or 2), —SF₅ or ahalogen atom, andn represents 0, 1 or 2,or an N-oxide thereof.[17] A compound represented by the formula (1-4):

whereinA^(3b) represents a nitrogen atom or ═CR^(9b)— (wherein R^(9b)represents a hydrogen atom or a halogen atom), represents an ethyl groupor a cyclopropylmethyl group,R^(1b) represents an ethyl group or a cyclopropylmethyl group,R^(3b) represents a C1-C6 alkyl group optionally substituted by one ormore halogen atoms, —OR^(20b) (wherein R^(20b) represents a C1-C6 alkylgroup optionally substituted by one or more halogen atoms),—S(O)_(m)R^(21b) (wherein R^(21b) represents a C1-C6 alkyl groupoptionally substituted by one or more halogen atoms, m represents 0, 1or 2), a halogen atom or a hydrogen atom,R^(5b) represents a C1-C6 haloalkyl group, —OR^(22b) (wherein R^(22b)represents a C1-C6 haloalkyl group), —S(O)_(m)R^(23b) (wherein R^(23b)represents a C1-C6 haloalkyl group, m represents 0, 1 or 2), —SF₅ or, ahalogen atom, andn represents 0, 1 or 2,or an N-oxide thereof.[18] A compound represented by the formula (1-5):

whereinR^(70a) represents a hydrogen atom or a C2-C6 alkoxyalkyl groupoptionally substituted by one or more halogen atoms,A^(3a) represents a nitrogen atom or ═CR^(9a)—,R^(1a) represents a C1-C6 alkyl group optionally substituted by one ormore atoms or groups selected from the group consisting of a halogenatom and a cyclopropyl group (wherein the cyclopropyl group isoptionally substituted by one or more halogen atoms or one or more C1-C3alkyl groups), a C2-C6 alkenyl group optionally substituted by one ormore halogen atoms or a C2-C6 alkynyl group optionally substituted byone or more halogen atoms,R^(2a) and R^(4a) are the same or different and each represents ahalogen atom or a hydrogen atom,R^(3a) represents a C1-C6 alkyl group optionally substituted by one ormore halogen atoms, a C2-C6 alkenyl group optionally substituted by oneor more halogen atoms, a C2-C6 alkynyl group optionally substituted byone or more halogen atoms, 5- or 6-membered aromatic heterocyclic group(wherein the 5- or 6-membered aromatic heterocyclic group is optionallysubstituted by one or more atoms or groups selected from the groupconsisting of a halogen atom, a C1-C3 alkyl group optionally substitutedby one or more halogen atoms, and C1-C3 alkoxy group optionallysubstituted by one or more halogen atoms), —OR^(20a) (wherein R^(20a)represents a C1-C6 alkyl group optionally substituted by one or morehalogen atoms), —S(O)_(m)R^(21a) (wherein R^(21a) represents a C1-C6alkyl group optionally substituted by one or more halogen atoms, mrepresents 0, 1 or 2), a cyano group, a nitro group, a halogen atom or ahydrogen atom,R^(5a) represents a C1-C6 alkyl group optionally substituted by one ormore halogen atoms, —OR^(22a) (wherein R^(22a) represents a C1-C6 alkylgroup optionally substituted by one or more halogen atoms),—S(O)_(m)R^(23a) (wherein R^(23a) represents a C1-C6 alkyl groupoptionally substituted by one or more halogen atoms, m represents 0, 1or 2), —SF₅ or a halogen atom,R^(9a) represents a C1-C6 alkyl group optionally substituted by one ormore halogen atoms, —OR^(24a) (wherein R^(24a) represents a C1-C6 alkylgroup optionally substituted by one or more halogen atoms),—S(O)_(m)R^(25a) (wherein R^(25a) represents a C1-C6 alkyl groupoptionally substituted by one or more halogen atoms, m represents 0, 1or 2), a halogen atom or a hydrogen atom, andn represents 0, 1 or 2,or an N-oxide thereof.[19] A pest control composition comprising a compound according to anyone of the above [1] to [18] and an inert carrier.[20] A method for controlling a pest, which comprises applying aneffective amount of the compound according to any one of the above [1]to [18] to the pest or a habitat of the pest.[21] A compound represented by the formula (M3-1):

whereinA^(1a) represents —NR^(7a)—, an oxygen atom or a sulfur atom,A^(3a) represents a nitrogen atom or ═CR^(9a)—,R^(1a) represents a C1-C6 alkyl group optionally substituted by one ormore atoms or groups selected from the group consisting of a halogenatom and a cyclopropyl group (wherein the cyclopropyl group isoptionally substituted by one or more halogen atoms or one or more C1-C3alkyl groups), a C2-C6 alkenyl group optionally substituted by one ormore halogen atoms or a C2-C6 alkynyl group optionally substituted byone or more halogen atoms,R^(2a) and R^(4a) are the same or different and each represents ahalogen atom or a hydrogen atom,R^(3a) represents a C1-C6 alkyl group optionally substituted by one ormore halogen atoms, a C2-C6 alkenyl group optionally substituted by oneor more halogen atoms, a C2-C6 alkynyl group optionally substituted byone or more halogen atoms, 5- or 6-membered aromatic heterocyclic group(wherein the 5- or 6-membered aromatic heterocyclic group is optionallysubstituted by one or more atoms or groups selected from the groupconsisting of a halogen atom, a C1-C3 alkyl group optionally substitutedby one or more halogen atoms, and a C1-C3 alkoxy group optionallysubstituted by one or more halogen atoms), —OR^(20a) (wherein R^(20a)represents a C1-C6 alkyl group optionally substituted by one or morehalogen atoms), —S(O)_(m)R^(2a) (wherein R^(21a) represents a C1-C6alkyl group optionally substituted by one or more halogen atoms, mrepresents 0, 1 or 2), a cyano group, a nitro group, a halogen atom or ahydrogen atom,R^(5a) represents a C1-C6 alkyl group optionally substituted by one ormore halogen atoms, —OR^(22a) (wherein R^(22a) represents a C1-C6 alkylgroup optionally substituted by one or more halogen atoms),—S(O)_(m)R^(23a) (wherein R^(23a) represents a C1-C6 alkyl groupoptionally substituted by one or more halogen atoms, m represents 0, 1or 2), —SF₅ or a halogen atom,R^(7a) represents a C1-C6 alkyl group optionally substituted by one ormore halogen atoms, a C3-C6 alkenyl group optionally substituted by oneor more halogen atoms, a C3-C6 alkynyl group optionally substituted byone or more halogen atoms, or a C1-C6 alkyl group substituted by one 5-or 6-membered aromatic heterocyclic group, (wherein the 5- or 6-memberedaromatic heterocyclic group is optionally substituted by one or moreatoms or groups selected from the group consisting of a halogen atom, aC1-C3 alkyl group optionally substituted by one or more halogen atoms,and a C1-C3 alkoxy group optionally substituted by one or more halogenatoms),R^(9a) represents a C1-C6 alkyl group optionally substituted by one ormore halogen atoms, —OR^(24a) (wherein R^(24a) represents a C1-C6 alkylgroup optionally substituted by one or more halogen atoms),—S(O)_(m)R^(25a) (wherein R^(25a) represents a C1-C6 alkyl groupoptionally substituted by one or more halogen atoms, m represents 0, 1or 2), a halogen atom or a hydrogen atom,n represents 0, 1 or 2, andor an N-oxide thereof.[22] A compound represented by the formula (M6-1):

whereinV² represents a halogen atom,A^(1a) represents —NR^(7a)—, an oxygen atom or a sulfur atom,A^(1a) represents a nitrogen atom or ═CR^(9a)—,R^(2a) and R^(4a) are the same or different and each represents ahalogen atom or a hydrogen atom,R^(3a) represents a C1-C6 alkyl group optionally substituted by one ormore halogen atoms, a C2-C6 alkenyl group optionally substituted by oneor more halogen atoms, a C2-C6 alkynyl group optionally substituted byone or more halogen atoms, 5- or 6-membered aromatic heterocyclic group(wherein the 5- or 6-membered aromatic heterocyclic group is optionallysubstituted by one or more atoms or groups selected from the groupconsisting of a halogen atom, a C1-C3 alkyl group optionally substitutedby one or more halogen atoms, and a C1-C3 alkoxy group optionallysubstituted by one or more halogen atoms), —OR^(20a) (wherein R^(20a)represents a C1-C6 alkyl group optionally substituted by one or morehalogen atoms), —S(O)_(m)R^(21a) (wherein R^(21a) represents a C1-C6alkyl group optionally substituted by one or more halogen atoms, mrepresents 0, 1 or 2), a cyano group, a nitro group, a halogen atom or ahydrogen atom,R^(5a) represents a C1-C6 alkyl group optionally substituted by one ormore halogen atoms, —OR^(22a) (wherein R^(22a) represents a C1-C6 alkylgroup optionally substituted by one or more halogen atoms),—S(O)_(m)R^(23a) (wherein R^(23a) represents a C1-C6 alkyl groupoptionally substituted by one or more halogen atoms, m represents 0, 1or 2), —SF₅ or a halogen atom,R^(7a) represents a C1-C6 alkyl group optionally substituted by one ormore halogen atoms, a C3-C6 alkenyl group optionally substituted by oneor more halogen atoms, a C3-C6 alkynyl group optionally substituted byone or more halogen atoms, or a C1-C6 alkyl group substituted by one 5-or 6-membered aromatic heterocyclic group, (wherein the 5- or 6-memberedaromatic heterocyclic group is optionally substituted by one or moreatoms or groups selected from the group consisting of a halogen atom, aC1-C3 alkyl group optionally substituted by one or more halogen atoms,and a C1-C3 alkoxy group optionally substituted by one or more halogenatoms), andR^(9a) represents a C1-C6 alkyl group optionally substituted by one ormore halogen atoms, —OR^(24a) (wherein R^(24a) represents a C1-C6 alkylgroup optionally substituted by one or more halogen-atoms),—S(O)_(m)R^(25a) (wherein R^(25a) represents a C1-C6 alkyl groupoptionally substituted by one or more halogen atoms, m represents 0, 1or 2), a halogen atom or a hydrogen atom,or an N-oxide thereof.[23] A compound represented by the formula (M20-1):

whereinV² represents a halogen atom,A^(1a) represents —NR^(7a)—, an oxygen atom or a sulfur atom,A^(3a) represents a nitrogen atom or ═CR^(9a)—,R^(2a) and R^(4a) are the same or different and each represents ahalogen atom or a hydrogen atom,R^(3a) represents a C1-C6 alkyl group optionally substituted by one ormore halogen atoms, a C2-C6 alkenyl group optionally substituted by oneor more halogen atoms, a C2-C6 alkynyl group optionally substituted byone or more halogen atoms, 5- or 6-membered aromatic heterocyclic group(wherein the 5- or 6-membered aromatic heterocyclic group is optionallysubstituted by one or more atoms or groups selected from the groupconsisting of a halogen atom, a C1-C3 alkyl group optionally substitutedby one or more halogen atoms, and a C1-C3 alkoxy group optionallysubstituted by one or more halogen atoms), —OR^(20a) (wherein R^(20a)represents a C1-C6 alkyl group optionally substituted by one or morehalogen atoms), —S(O)_(m)R^(21a) (wherein R^(21a) represents a C1-C6alkyl group optionally substituted by one or more halogen atoms, mrepresents 0, 1 or 2), a cyano group, a nitro group, a halogen atom or ahydrogen atom,R^(5a) represents a C1-C6 alkyl group optionally substituted by one ormore halogen atoms, —OR^(22a) (wherein R^(22a) represents a C1-C6 alkylgroup optionally substituted by one or more halogen atoms),—S(O)_(m)R^(23a) (wherein R^(23a) represents a C1-C6 alkyl groupoptionally substituted by one or more halogen atoms, m represents 0, 1or 2), —SF₅ or a halogen atom,R^(7a) represents a C1-C6 alkyl group optionally substituted by one ormore halogen atoms, a C3-C6 alkenyl group optionally substituted by oneor more halogen atoms, a C3-C6 alkynyl group optionally substituted byone or more halogen atoms, or a C1-C6 alkyl group substituted by one 5-or 6-membered aromatic heterocyclic group, (wherein the 5- or 6-memberedaromatic heterocyclic group is optionally substituted by one or moreatoms or groups selected from the group consisting of a halogen atom, aC1-C3 alkyl group optionally substituted by one or more halogen atoms,and a C1-C3 alkoxy group optionally substituted by one or more halogenatoms), andR^(9a) represents a C1-C6 alkyl group optionally substituted by one ormore halogen atoms, —OR^(24a) (wherein R^(24a) represents a C1-C6 alkylgroup optionally substituted by one or more halogen atoms),—S(O)_(m)R^(25a) (wherein R^(25a) represents a C1-C6 alkyl groupoptionally substituted by one or more halogen atoms, m represents 0, 1or 2), a halogen atom or a hydrogen atom,or an N-oxide thereof.

Effect of Invention

The present compound has an excellent controlling effect on pests and isuseful as an active ingredient of a pest control agent.

DESCRIPTION OF EMBODIMENTS

The “N-oxide” in the present compound means a compound wherein anitrogen atom constituting a ring in a heterocyclic group is oxidized.Examples of the “heterocyclic group” which can form the N-oxide in thepresent compound include a pyridine ring.

The groups used herein will be illustrated in detail by way of examples.

In the present application, the “Ca-Cb chain hydrocarbon group” means alinear or branched, saturated or unsaturated hydrocarbon group having ato b carbon atoms;

the “Ca-Cb alkyl group” means a linear or branched hydrocarbon grouphaving a to b carbon atoms;

the “Ca-Cb alkenyl group” means a linear or branched, unsaturatedhydrocarbon group having a to b carbon atoms and one or more doublebonds within the molecule;

the “Ca-Cb alkynyl group” means a linear or branched, unsaturatedhydrocarbon group having a to b carbon atoms and one or more triplebonds within the molecule;

the “Ca-Cb haloalkyl group” means a linear or branched alkyl grouphaving a to b carbon atoms, wherein the hydrogen atom(s) bound to thecarbon atom(s) is/are substituted by one or more halogen atoms, and whenthe group is substituted by two or more halogen atoms, these halogenatoms are the same or different from each other;

the Ca-Cb alkoxy group” means a linear or branched alkyl-O-group havinga to b carbon atoms;

the “Ca-Cb alkenyloxy group” means a linear or branched alkenyl-O-grouphaving a to b carbon atoms and one or more double bonds within themolecule;

the “Ca-Cb” alkynyloxy group” means, a linear or branchedalkynyl-O-group having a to b carbon atoms and one or more triple bondswithin the molecule;

the “Ca-Cb alkylsulfanyl group” means a linear or branched alkyl-S-grouphaving a to b carbon atoms;

the “Ca-Cb alkylsulfinyl group” means a linear or branchedalkyl-S(O)-group having a to b carbon atoms;

the “Ca-Cb alkylsulfonyl group” means a linear or branchedalkyl-S(O)₂-group having a to b carbon atoms;

the “Ca-Cb alkyl carbonyl group” means a linear or branchedalkyl-C(O)-group having a to b carbon atoms;

the “Ca-Cb alkoxycarbonyl group” means a linear or branchedalkyl-O—C(O)-group having a to b carbon atoms;

the “Ca-Cb alicyclic hydrocarbon group” means a cyclic nonaromatichydrocarbon group having a to b carbon atoms;

the “Ca-Cb cycloalkyl group” means a cyclic alkyl group having a to bcarbon atoms;

the “Ca-Cb alkylamino group” means a linear or branched alkyl-NH-grouphaving a to b carbon atoms;

the “Ca-Cb dialkylamino group” means a linear or branched dialkylaminogroup, wherein the alkyl groups have the same or different carbon atomsand the total number of carbon atoms is a to b;

the “Ca-Cb alkoxyalkyl group” means a linear or branched alkyl-O-alkylgroup, wherein the alkyl groups have the same or different carbon atomsand the total number of carbon atoms is a to b.

In the “optionally substituted by one or more atoms or groups selectedfrom Group X” used herein, when two or more atoms or groups selectedfrom Group X are present, these atoms or groups selected from Group Xare the same or different from each other.

In the “optionally substituted by one or more atoms or groups selectedfrom Group Y” used herein, when two or more atoms or groups selectedfrom Group Y are present, these atoms or groups selected from Group Yare the same or different from each other.

In the “optionally substituted by one or more atoms or groups selectedfrom Group Z” used herein, when two or more atoms or groups selectedfrom Group Z are present, these atoms or groups selected from Group Zare the same or different from each other.

In the “optionally substituted by one or more atoms or groups selectedfrom Group W” used herein, when two or more atoms or groups selectedfrom Group W are present, these atoms or groups selected from Group Ware the same or different from each other.

In the “optionally substituted by one or more halogen atoms” usedherein, when two or more halogen atoms are present, these halogen atomsare the same or different from each other.

The “halogen atom” in the present compound includes a fluorine atom, achlorine atom, a bromine atom and an iodine atom.

The “C1-C6 chain hydrocarbon group optionally substituted by one or moreatoms or groups selected from Group X” in the present compound means alinear or branched hydrocarbon group having 1 to 6 carbon atoms, whereinthe hydrogen atom(s) bound to the carbon atom(s) is/are optionallysubstituted by one or more atoms or groups selected from Group X, andwhen the group is substituted by two or more atoms or groups selectedfrom Group X, these atoms or groups are the same or different from eachother.

Examples of the “C1-C6 chain hydrocarbon group optionally substituted byone or more atoms or groups selected from Group X” in the presentcompound include C1-C6 alkyl groups optionally substituted by one ormore atoms or groups selected from Group X, such as a methyl group, anethyl group, a propyl group, an isopropyl group, a butyl group, anisobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, aneopentyl group, a hexyl group, a methoxymethyl group, an ethoxymethylgroup, a propyloxymethyl group, an isopropyloxymethyl group, abutyloxymethyl group, a sec-butyloxymethyl group, a tert-butyloxymethylgroup, a 2-methoxyethyl group, a 2-ethoxyethyl group, a 2-propyloxyethylgroup, a 2-isopropyloxyethyl group, a 2-butyloxyethyl group, a2-sec-butyloxyethyl group, a 2-tert-butyloxyethyl group, atrifluoromethyl group, a trichloromethyl group, a 2-fluoroethyl group, a2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group and apentafluoroethyl group, a methylsulfanylethyl group, aethylsulfanylethyl group, a methylsulfinylethyl group, amethylsulfonylethyl group, a 2-hydroxy ethyl group, a cyclopropylmethylgroup, a 1-methylcyclopropylmethyl group, a2,2-difluorocyclopropylmethyl group, and the like;

C2-C6 alkenyl groups optionally substituted by one or more atoms orgroups selected from Group X, such as a vinyl group, a 1-propenyl group,a 2-propenyl group, a 1-methyl vinyl group, a 2-methyl-1-propenyl group,a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenylgroup, a 1-hexenyl group, a 1,1-difluoroallyl group, a pentafluoroallylgroup, and the like; andC2-C6 alkynyl groups optionally substituted by one or more atoms orgroups selected from Group X, such as an ethynyl group, a propargylgroup, a 2-butynyl group, a 3-butynyl group, a 1-pentynyl group, a1-hexynyl group and a 4,4,4-trifluoro-2-butynyl group, and the like;which is selected depending on a given range of carbon atoms.

The “C3-C6 alicyclic hydrocarbon group optionally substituted by one ormore atoms or groups selected from Group Y” in the present compoundmeans a cyclic non-aromatic hydrocarbon group having 3 to 6 carbonatoms, wherein the hydrogen atom(s) bound to the carbon atom(s) is/areoptionally substituted by one or more atoms or groups selected fromGroup Y, and when the group is substituted by two or more atoms orgroups selected from Group Y, these atoms or groups are the same ordifferent from each other.

Examples of the “C3-C6 alicyclic hydrocarbon group optionallysubstituted by one or more atoms or groups selected from Group Y” in thepresent compound include a cyclopropyl group, a cyclobutyl group, acyclopentyl group, a cyclohexyl group, a 1-cyclohexenyl group, a2-cyclohexenyl group, a 3-cyclohexenyl group, a 1-methylcyclohexylgroup, a 2-methylcyclohexyl group, a 3-methylcyclohexyl group, a4-methylcyclohexyl group, a 2-methoxycyclohexyl group, a3-methoxycyclohexyl group, a 4-methoxycyclohexyl group, a1-fluorocyclohexyl group, a 2-fluorocyclohexyl group, a3-fluorocyclohexyl group, and a 4-fluorocyclohexyl group.

The “C1-C6 chain hydrocarbon group optionally substituted by one or morehalogen atoms” in the present compound means a linear or branchedhydrocarbon group having 1 to 6 carbon atoms, wherein the hydrogenatom(s) bound to the carbon atom(s) is/are optionally substituted by oneor more halogen atoms, and when the group is substituted by two or morehalogen atoms, these halogen atoms are the same or different from eachother.

Examples of the “C1-C6 chain hydrocarbon group optionally substituted byone or more halogen atoms” in the present compound include C1-C6 alkylgroups optionally substituted by one or more halogen atoms such as amethyl group, an ethyl group, a propyl group, an isopropyl group, abutyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, apentyl group, a neopentyl group, a hexyl group, a trifluoromethyl group,a trichloromethyl group, a 2-fluoroethyl group, a 2,2-difluoroethylgroup, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, aheptafluoroisopropyl group, and the like;

C2-C6 alkenyl groups optionally substituted by one or more halogen atomssuch as a vinyl group, a 1-propenyl group, a 2-propenyl group, a1-methylvinyl group, a 2-methyl-1-propenyl group, a 1-butenyl group, a2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 1-hexenylgroup, a 1,1-difluoroallyl group, a pentafluoroallyl group, and thelike;C2-C6 alkynyl groups optionally substituted by one or more halogen atomssuch as an ethynyl group, a propargyl group, a 2-butynyl group, a3-butynyl group, a 1-pentynyl group, a 1-hexynyl group, a4,4,4-trifluoro-2-butynyl group, and the like; which is selecteddepending on a given range of carbon atoms.

The “phenyl group optionally substituted by one or more atoms or groupsselected from Group Z” in the present compound means a phenyl group,wherein the hydrogen atom(s) bound to the carbon atom(s) is/areoptionally substituted by one or more atoms or groups selected fromGroup Z, and when the group is substituted by two or more atoms orgroups selected from Group Z, these atoms or groups are the same ordifferent from each other.

Examples of the “phenyl group optionally substituted by one or moreatoms or groups selected from Group Z” in the present compound include aphenyl group, a 2-fluorophenyl group, a 3-fluorophenyl group, a4-fluorophenyl group, a 2,3-difluorophenyl group, a 2,4-difluorophenylgroup, a 2,5-difluorophenyl group, a 2,6-difluorophenyl group, a3,4-difluorophenyl group, a 3,5-difluorophenyl group, a2,3,4,5,6-pentafluorophenyl group, a 2-chlorophenyl group, a3-chlorophenyl group, a 4-chlorophenyl group, a 2-bromophenyl group, a3-bromophenyl group, a 4-bromophenyl group, a 2-iodophenyl group, a3-iodophenyl group, a 4-iodophenyl group, a 2-trifluoromethyl phenylgroup, a 3-trifluoromethylphenyl group, a 4-trifluoromethylphenyl group,a 2-trifluoromethoxyphenyl group, a 3-trifluoromethoxyphenyl group, a4-trifluoromethoxyphenyl group, a 2-trifluoromethylsulfanylphenyl group,a 3-trifluoromethylsulfanylphenyl group, a4-trifluoromethylsulfanylphenyl group, a 4-methoxycarbonylphenyl group,a 4-nitrophenyl group, a 4-cyanophenyl group, a 4-methylaminophenylgroup, a 4-dimethylaminophenyl group, a 4-methylsulfinylphenyl group, a4-methylsulfonylphenyl group, a 4-acetylphenyl group and a4-methoxycarbonylphenyl group.

The “heterocyclic group” in the present compound means a residue of aheterocyclic compound having one or more nitrogen atoms, oxygen atoms orsulfur atoms in addition to carbon atoms in the ring structure.

The “5-membered heterocyclic group” in the present compound means a5-membered aromatic heterocyclic group or 5-membered non-aromaticheterocyclic group, and the “6-membered heterocyclic group” means a6-membered aromatic heterocyclic group or a 6-membered non-aromaticheterocyclic group.

The “heterocyclic group” in the “5- or 6-membered heterocyclic groupoptionally substituted by one or more atoms or groups selected fromGroup Z” in the present compound means a residue of a heterocycliccompound having one or more nitrogen atoms, oxygen atoms or sulfur atomsin addition to carbon atoms in the ring structure, wherein the group hastwo or more atoms or groups selected from Group Z, these atoms or groupsare the same or different from each other.

The “5- or 6-membered heterocyclic group” in the present compound meansa 5- or 6-membered aromatic heterocyclic group, or a 5- or 6-memberednon-aromatic heterocyclic group.

Examples of the “5- or 6-membered heterocyclic group optionallysubstituted by one or more atoms or groups selected from Group Z” in thepresent compound include 5 or 6-membered non-aromatic heterocyclicgroups optionally substituted by one or more atoms or groups selectedfrom Group Z, such as a pyrrolidin-1-yl group, a3,3,4,4-tetrafluoropyrrolidin-1-yl group, a tetrahydrofuran-2-yl group,a piperidyl group, a morpholyl group, a thiomorpholyl group, and thelike;

5- or 6-membered aromatic heterocyclic groups optionally substituted byone or more atoms or groups selected from Group Z, such as a 2-pyrrolygroup, a 2-furyl group, a 3-furyl group, a 5-pyrazolyl group, a4-pyrazolyl group, a 1-pyrroly group, a 1-methyl-2-pyrroly group, a2-methylsulfanyl-1-pyrroly group, a 2-methylsulfinyl-1-pyrroly group, a2-methylsulfonyl-1-pyrroly group, a 2-methylamino-1-pyrroly group, a2-dimethylamino-1-pyrroly group, a 5-bromo-2-furyl group, a5-nitro-2-furyl group, a 5-cyano-2-furyl group, a 5-methoxy-2-furylgroup, a 5-acetyl-2-furyl group, a 5-methoxycarbonyl-2-furyl group, a2-methyl-3-furyl group, a 2,5-dimethyl-3-furyl group, a2,4-dimethyl-3-furyl group, a 5-methyl-2-thienyl group, a3-methyl-2-thienyl group, a 1-methyl-3-trifluoromethyl-5-pyrazolylgroup, a 5-chloro-1,3-dimethyl-4-pyrazolyl group, pyrazol-1-yl group, a3-chloro-pyrazol-1-yl group, a 3-bromopyrazol-1-yl group, a4-chloropyrazol-1-yl group, a 4-bromopyrazol-1-yl group, animidazole-1-yl group, a 1,2,4-triazol-1-yl group, a3-chloro-1,2,4-triazol-1-yl group, a 1,2,3,4-tetrazol-1-yl group, a1,2,3,5-tetrazol-1-yl group, a 2-thienyl group, a 3-thienyl group, a3-trifluoromethyl-1,2,4-triazol-1-yl group, a 4-trifluoromethylpyrazol-1-yl group, pyrazinyl group, a 4-pyrimidinyl group, a5-pyrimidinyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridylgroup, a 3-fluoro-2-pyridyl group, a 4-fluoro-2-pyridyl group, a5-fluoro-2-pyridyl group, a 6-fluoro-2-pyridyl group, a 2-pyrimidinylgroup, a 3-chloro-5-trifluoromethylpyridin-2-yl group, a5-trifluoromethylpyridin-2-yl group, and the like.

Examples of the “C1-C6 chain hydrocarbon group substituted by one phenylgroup (wherein the phenyl group is optionally substituted by one or moreatoms or groups selected from Group Z)” in the present compound includea phenylmethyl group, a 4-chlorophenylmethyl group and a4-trifluoromethyl phenylmethyl group, and the like. When the group hastwo or more atoms or groups selected from Group Z, these atoms or groupsare the same or different from each other.

Examples of the “C1-C6 chain hydrocarbon group substituted by one 5- or6-membered heterocyclic group (wherein the 5- or 6-membered heterocyclicgroup is optionally substituted by one or more atoms or groups selectedfrom Group Z)” in the present compound include 5 or 6-memberednon-aromatic heterocyclic groups such as a tetrahydrofuran-2-ylmethylgroup, a tetrahydropyran-2-ylmethyl group, a tetrahydropyran-3-ylmethylgroup, and the like;

5- or 6-membered aromatic heterocyclic groups such as athiazol-5-ylmethyl group, a 2-chlorothiazol-5-ylmethyl group, apyridin-3-ylmethyl group, a 6-chloropyridin-3-ylmethyl group, a6-trifluoromethylpyridin-3-ylmethyl group, and the like. When the grouphas two or more atoms or groups selected from Group Z, these atoms orgroups are the same or different from each other.

Examples of the “C1-C6 alkyl group substituted by one 5- or 6-memberedaromatic heterocyclic group (wherein the 5- or 6-membered aromaticheterocyclic group is optionally substituted by one or more atoms orgroups selected from the group consisting of a halogen atom, a C1-C3alkyl group optionally substituted by one or more halogen atoms, and aC1-C3 alkoxy group optionally substituted by one or more halogen atoms)”in the present compound include a thiazol-5-ylmethyl group, a2-chlorothiazol-5-ylmethyl group, a pyridin-3-ylmethyl group, a6-chloropyridin-3-ylmethyl group, a 6-trifluoromethylpyridin-3-ylmethylgroup, and the like.

Examples of the “5- or 6-membered aromatic heterocyclic group (whereinthe 5- or 6-membered aromatic heterocyclic group is optionallysubstituted by one or more atoms or groups selected from the groupconsisting of a halogen atom, a C1-C3 alkyl group optionally substitutedby one or more halogen atoms, and a C1-C3 alkoxy group optionallysubstituted by one or more halogen atoms)” in the present compoundinclude, a 2-pyrroly group, a 2-furyl group, a 3-furyl group, a5-pyrazolyl group, a 4-pyrazolyl group, a 1-pyrroly group, a1-methyl-2-pyrroly group, a 5-bromo-2-furyl group, a 5-methoxy-2-furylgroup, a 2-methyl-3-furyl group, a 2,5-dimethyl-3-furyl group, a2,4-dimethyl-3-furyl group, a 5-methyl-2-thienyl group, a3-methyl-2-thienyl group, a 1-methyl-3-trifluoromethyl-5-pyrazolylgroup, a 5-chloro-1,3-dimethyl-4-pyrazolyl group, a pyrazol-1-yl group,a 3-chloro-pyrazol-1-yl group, a 3-bromopyrazol-1-yl group, a4-chloropyrazol-1-yl group, a 4-bromopyrazol-1-yl group, animidazole-1-yl group, a 1,2,4-triazol-1-yl group, a3-chloro-1,2,4-triazol-1-yl group, a 1,2,3,4-tetrazol-1-yl group, a1,2,3,5-tetrazol-1-yl group, a 2-thienyl group, a 3-thienyl group, a3-trifluoromethyl-1,2,4-triazol-1-yl group, a 4-trifluoromethylpyrazol-1-yl group, a pyrazinyl group, a 4-pyrimidinyl group, a5-pyrimidinyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridylgroup, a 3-fluoro-2-pyridyl group, a 4-fluoro-2-pyridyl group, a5-fluoro-2-pyridyl group, a 6-fluoro-2-pyridyl group, a 2-pyrimidinylgroup, a 3-chloro-5-trifluoromethylpyridin-2-yl group, a5-trifluoromethylpyridin-2-yl group, and the like.

Examples of the “C1-C6 alkyl group optionally substituted by one or moreatoms or groups selected from the group consisting of a halogen atom anda cyclopropyl group (wherein the cyclopropyl group is optionallysubstituted by one or more halogen atoms or one or more C1-C3 alkylgroups)” in the present compound include a methyl group, an ethyl group,a propyl group, an isopropyl group, butyl group, an isobutyl group, asec-butyl group, a tert-butyl group, a pentyl group, a neopentyl group,a hexyl group, a trifluoromethyl group, a trichloromethyl group, a2-fluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethylgroup, a pentafluoroethyl group, a heptafluoroisopropyl group, acyclopropylmethyl group, a 2-cyclopropylethyl group, a1-cyclopropylethyl group, a 1-methylcyclopropylmethyl group, and thelike.

Examples of the “C1-C6 chain hydrocarbon group optionally substituted byone or more atoms or groups selected from Group W” in the presentcompound include C1-C6 alkyl groups optionally substituted by one ormore atoms or groups selected from Group W, such as a methyl group, anethyl group, a propyl group, an isopropyl group, a butyl group, anisobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, aneopentyl group, a hexyl group, a trifluoromethyl group, atrichloromethyl group, a 2-fluoroethyl group, a 2,2-difluoroethyl group,a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, a methoxymethylgroup, an ethoxymethyl group, a propyloxymethyl group, anisopropyloxymethyl group, a butyloxymethyl group, a sec-butyloxymethylgroup, an isobutyloxymethyl group, a tert-butyloxymethyl group, amethoxyethyl group, an ethoxyethyl group, a propyloxyethyl group, anisopropyloxyethyl group, a butyloxyethyl group, a sec-butyloxyethylgroup, an isobutyloxyethyl group, a tert-butyloxyethyl group, amethylsulfanylethyl group, an ethylsulfanylethyl group, amethylsulfinylethyl group, methylsulfonylethyl group, amethoxycarbonylmethyl group, a methoxycarbonylethyl group, a2-cyanoethyl group, a 2-oxopropyl, a cyclopropylmethyl group, acyclohexylmethyl group, and the like;

C2-C6 alkenyl groups optionally substituted by one or more atoms orgroups selected from Group W, such as a vinyl group, a 1-propenyl group,a 2-propenyl group, a 1-methylvinyl group, a 2-methyl-1-propenyl group,a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenylgroup, a 1-hexenyl group, a 1,1-difluoroallyl group, pentafluoroallylgroup, and the like;C2-C6 alkynyl groups optionally substituted by one or more atoms orgroups selected from Group W, such as an ethynyl group, a propargylgroup, a 2-butynyl group, a 3-butynyl group, a 1-pentynyl group, a1-hexynyl group, a 4,4,4-trifluoro-2-butynyl group, and the like. Whenthe group has two or more atoms or groups selected from Group W, theseatoms or groups are the same or different from each other.

Examples of the “C1-C6 alkoxy group optionally substituted by one ormore halogen atoms” in the present compound include a methoxy group, atrifluoromethoxy group, an ethoxy group, a 2,2,2-trifluoroethoxy group,a propyloxy group, an isopropyloxy group, a butyloxy group, anisobutyloxy group, a sec-butyloxy group, a tert-butyloxy group, apentyloxy group, a hexyloxy group, and the like.

Examples of the “C2-C6 alkenyloxy group substituted by one or morehalogen atoms” in the present compound include a 2-propenyloxy group, a2-methyl-2-propenyloxy group, a 2-butenyloxy group, a 3-butenyloxygroup, a 2-pentenyloxy group, a 2-hexenyloxy group, a3,3-difluoroallyloxy group, a 3,3-dichloro allyloxy group, and the like.

Examples of the “C2-C6 alkynyloxy group optionally substituted by one ormore halogen atoms” in the present compound include a propargyloxygroup, a 2-butynyloxy group, a 3-butynyloxy group, a 2-pentynyloxygroup, a 2-hexynyloxy group, a 4,4,4-trifluoro-2-butynyl oxy group, andthe like.

Examples of the “C1-C6 alkylsulfanyl group optionally substituted by oneor more halogen atoms” in the present compound include a methylsulfanylgroup, an ethylsulfanyl group, a propylsulfanyl group, anisopropylsulfanyl group, a butylsulfanyl group, a pentylsulfanyl group,a hexylsulfanyl group, a trifluoromethylsulfanyl group, a2,2,2-trifluoroethylsulfanyl group, a pentafluoroethylsulfanyl group,and the like.

Examples of the “C1-C6 alkylsulfinyl group optionally substituted by oneor more halogen atoms” in the present compound include a methylsulfinylgroup, an ethylsulfinyl group, a propylsulfinyl group, anisopropylsulfinyl group, butylsulfinyl group, a pentylsulfinyl group, ahexylsulfinyl group, a trifluoromethylsulfinyl group, a2,2,2-trifluoroethylsulfinyl group, a pentafluoroethylsulfinyl group,and the like.

Examples of the “C1-C6 alkylsulfonyl group optionally substituted by oneor more halogen atoms” in the present compound include a methylsulfonylgroup, an ethylsulfonyl group, a propylsulfonyl group, anisopropylsulfonyl group, a butylsulfonyl group, a pentylsulfonyl group,a hexylsulfonyl group, a trifluoromethylsulfonyl group, a2,2,2-trifluoroethylsulfonyl group, a pentafluoroethylsulfonyl group,and the like.

Examples of the “C2-C6 alkylcarbonyl group optionally substituted by oneor more halogen atoms” in the present compound include an acetyl group,a propionyl group, a butyryl group, a pentanoyl group, a hexanoyl group,a trifluoroacetyl group, and the like.

Examples of the “C2-C6 alkoxycarbonyl group optionally substituted byone or more halogen atoms” in the present compound include amethoxycarbonyl group, an ethoxycarbonyl group, a propyloxycarbonylgroup, a butyloxycarbonyl group, a pentyloxycarbonyl group, atert-butyloxycarbonyl group, a 2,2,2-trifluoroethyloxycarbonyl group,and the like.

Examples of the “C1-C6 alkylamino group optionally substituted by one ormore halogen atoms” in the present compound include a methylamino group,an ethylamino group, a 2,2,2-trifluoroethylamino group, a propylaminogroup, an isopropylamino group, a butylamino group, and the like.

Examples of the “C2-C8 dialkylamino group optionally substituted by oneor more halogen atoms” in the present compound include a dimethylaminogroup, a diethylamino group, a bis(2,2,2-trifluoroethyl)amino group, adipropylamino group, and the like.

Examples of the “C3-C6′ cycloalkyl group optionally substituted by oneor more halogen atoms” in the present compound include a cyclopropylgroup, a 2,2-difluorocyclopropyl group, a 2,2-dichlorocyclopropyl group,a 2,2-dibromocyclopropyl group, a cyclobutyl group, a cyclopentyl group,a cyclohexyl group, and the like.

Examples of the “C3-C6 cycloalkyl group optionally substituted by one ormore halogen atoms or one or more C1-C3 alkyl groups” in the presentcompound include a cyclopropyl group, a 1-methylcyclopropyl group, a2-methylcyclopropyl group, a 1-fluorocyclopropyl group, a2,2-difluorocyclopropyl group, a 2,2-dichlorocyclopropyl group, a2,2-dibromocyclopropyl group, a cyclobutyl group, a cyclopentyl group, acyclohexyl group, and the like.

Examples of the “C2-C6 alkyl group” in the present compound include anethyl group, a propyl group, an isopropyl group, a butyl group, anisobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, aneopentyl group, a hexyl group, and the like.

The “C1-C6 haloalkyl group” in the present compound means a linear orbranched hydrocarbon group having 1 to 6 carbon atoms, wherein thehydrogen atom(s) bound to the carbon atom(s) is/are substituted by oneor more halogen atoms, and when the group is substituted by two or morehalogen atoms, these halogen atoms are the same or different from eachother.

Examples of the “C1-C6 haloalkyl group” in the present compound includea fluoro methyl group, a chloromethyl group, a bromomethyl group, aniodomethyl group, a difluoromethyl group, a dichloromethyl group, atrifluoromethyl group, a chlorodifluoromethyl group, abromodifluoromethyl group, a trichloromethyl group, a 2-fluoroethylgroup, a 2-chloroethyl group, a 2-bromoethyl group, a 2,2-difluoroethylgroup, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, aheptafluoropropyl group, a heptafluoroisopropyl group, and the like.

Examples of the “C4-C9 cyclopropylalkyl group (wherein thecyclopropyl-group is optionally substituted by one or more halogen atomsor one or more C1-C3 alkyl groups)” in the present compound include acyclopropylmethyl group, a 2-cyclopropylethyl group, a1-cyclopropylethyl group, a 1-methylcyclopropyl group, and the like.

Examples of the “C1-C6 perfluoroalkyl group” in the present compoundinclude a trifluoromethyl group, a pentafluoroethyl group, aheptafluoropropyl group, a heptafluoroisopropyl group, and the like.

Examples of the “C1-C6 alkyl group optionally substituted by one or morehalogen atoms” in the present compound include a methyl group, an ethylgroup, a propyl group, an isopropyl group, butyl group, an isobutylgroup, a sec-butyl group, a tert-butyl group, a pentyl group, aneopentyl group, a hexyl group, a fluoromethyl group, a chloromethylgroup, a bromomethyl group, an iodomethyl group, a difluoromethyl group,a dichloromethyl group, a trifluoromethyl group, a chlorodifluoromethylgroup, a bromodifluoromethyl group, a trichloromethyl group, a2-fluoroethyl group, a 2-chloroethyl group, a 2-bromoethyl group, a2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, apentafluoroethyl group, a heptafluoropropyl group, aheptafluoroisopropyl group, and the like.

Examples of the “C2-C6 alkenyl group optionally substituted by one ormore halogen atoms” in the present compound include a vinyl group, a1-propenyl group, a 2-propenyl group, a 1-methyl vinyl group, a2-methyl-1-propenyl group, a 1-butenyl group, a 2-butenyl group, a3-butenyl group, a 1-pentenyl group, a 1-hexenyl group, a1,1-difluoroallyl group, a pentafluoroallyl group, and the like.

Examples of the “C2-C6 alkynyl group optionally substituted by one ormore halogen atoms” in the present compound include an ethynyl group, apropargyl group, a 2-butynyl group, a 3-butynyl group, a 1-pentynylgroup, a 1-hexynyl group, a 4,4,4-trifluoro-2-butynyl group, and thelike.

Examples of the “C3-C6 alkenyl group optionally substituted by one ormore halogen atoms” in the present compound include a 1-propenyl group,a 2-propenyl group, a 1-methyl vinyl group, a 2-methyl-1-propenyl group,a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenylgroup, a 1-hexenyl group, a 1,1-difluoroallyl group, a pentafluoroallylgroup, and the like.

Examples of the “C3-C6 alkynyl group optionally substituted by one ormore halogen atoms” in the present compound include a propargyl group, a2-butynyl group, a 3-butynyl group, a 1-pentynyl group, a 1-hexynylgroup, a 4,4,4-trifluoro-2-butynyl group, and the like.

Examples of the “C2-C6 alkoxyalkyl group optionally substituted by oneor more halogen atoms” in the present compound include a methoxymethylgroup, an ethoxymethyl group, a 1-(methoxy)ethyl group, a2-(methoxy)ethyl group, a 1-(ethoxy)ethyl group, a 2-(ethoxy)ethylgroup, a 2,2,2-trifluoroethoxymethyl group, and the like.

Examples of the “pyridyl group (wherein the pyridyl group is optionallysubstituted by one or more atoms or substituents selected from the groupconsisting of a halogen atom, a C1-C3 alkyl group optionally substitutedby one or more halogen atoms, and a C1-C3 alkoxy group optionallysubstituted by one or more halogen atoms)” in the present compoundinclude a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a5-trifluoromethyl-2-pyridyl group, a3-chloro-5-trifluoromethyl-2-pyridyl group, and the like.

Examples of the “pyrimidinyl group (wherein the pyrimidinyl group isoptionally substituted by one or more atoms or substituents selectedfrom the group consisting of a halogen atom, a C1-C3 alkyl groupoptionally substituted by one or more halogen atoms, and a C1-C3 alkoxygroup optionally substituted by one or more halogen atoms)” in thepresent compound include a 2-pyrimidinyl group, a 4-pyrimidinyl group, a5-pyrimidinyl group, a 2-chloro-4-pyrimidinyl group, and the like.

Examples of the “C1-C6 alkyl group substituted by one thiazolyl group(wherein the thiazolyl group is optionally substituted by one or moreatoms or substituents selected from the group consisting of a halogenatom, a C1-C3 alkyl group optionally substituted by one or more halogenatoms, and a C1-C3 alkoxy group optionally substituted by one or morehalogen atoms)” in the present compound include a (thiazol-5-yl)methylgroup, a (2-chlorothiazol-5-yl)methyl group, a1-(2-chlorothiazol-5-yl)ethyl group, and the like.

Examples of the “C1-C6 alkyl group substituted by one pyridyl group(wherein the pyridyl group is optionally substituted by one or moreatoms or substituents selected from the group consisting of a halogenatom, a C1-C3 alkyl group optionally substituted by one or more halogenatoms, and a C1-C3 alkoxy group optionally substituted by one or morehalogen atoms)” in the present compound include a (pyridin-5-yl)methylgroup, a (2-chloropyridin-5-yl)methyl group, a1-(2-chloropyridin-5-yl)ethyl group, a(2-trifluoromethylpyridin-5-yl)methyl group, and the like.

Examples of the present compound include the following compounds:

A compound represented by the formula (1-1):

whereinA^(1a) represents —NR^(7a)—, an oxygen atom or a sulfur atom,A^(3a) represents a nitrogen atom or ═CR^(9a)—,R^(1a) represents a C1-C6 alkyl group optionally substituted by one ormore atoms or groups selected from the group consisting of a halogenatom and a cyclopropyl group (wherein the cyclopropyl group isoptionally substituted by one or more halogen atoms or one or more C1-C3alkyl groups), a C2-C6 alkenyl group optionally substituted by one ormore halogen atoms or a C2-C6 alkynyl group optionally substituted byone or more halogen atoms,R^(2a) and R^(4a) are the same or different and each represents ahalogen atom or a hydrogen atom,R^(3a) represents a C1-C6 alkyl group optionally substituted by one ormore halogen atoms, a C2-C6 alkenyl group optionally substituted by oneor more halogen atoms, a C2-C6 alkynyl group optionally substituted byone or more halogen atoms, 5- or 6-membered aromatic heterocyclic group(wherein the 5- or 6-membered aromatic heterocyclic group is optionallysubstituted by one or more atoms or substituents selected from the groupconsisting of a halogen atom, a C1-C3 alkyl group optionally substitutedby one or more halogen atoms, and a C1-C3 alkoxy group optionallysubstituted by one or more halogen atoms), —OR^(20a) (wherein R^(20a)represents a C1-C6 alkyl group optionally substituted by one or morehalogen atoms), —S(O)_(m)R^(2a) (wherein R^(21a) represents a C1-C6alkyl group optionally substituted by one or more halogen atoms, mrepresents 0, 1 or 2), a cyano group, a nitro group, a halogen atom or ahydrogen atom,R^(5a) represents a C1-C6 alkyl group optionally substituted by one ormore halogen atoms, —OR^(22a) (wherein R^(22a) represents a C1-C6 alkylgroup optionally substituted by one or more halogen atoms),—S(O)_(m)R^(23a) (wherein R^(23a) represents a C1-C6 alkyl groupoptionally substituted by one or more halogen atoms, m represents 0, 1or 2), —SF₅ or a halogen atom,R^(7a) represents a C1-C6 alkyl group optionally substituted by one ormore halogen atoms, a C3-C6 alkenyl group optionally substituted by oneor more halogen atoms, a C3-C6 alkynyl group optionally substituted byone or more halogen atoms or a C1-C6 alkyl group substituted by one 5-or 6-membered aromatic heterocyclic group (wherein the 5- or 6-memberedaromatic heterocyclic group is optionally substituted by one or moreatoms or substituents selected from the group consisting of a halogenatom, a C1-C3 alkyl group optionally substituted by one or more halogenatom, and a C1-C3 alkoxy group optionally substituted by one or morehalogen atoms),R^(9a) represents a C1-C6 alkyl group optionally substituted by one ormore halogen atoms, —OR^(24a) (wherein R^(24a) represents a C1-C6 alkylgroup optionally substituted by one or more halogen atoms),—S(O)_(m)R^(25a) (wherein R^(25a) represents a C1-C6 alkyl groupoptionally substituted by one or more halogen atoms, m represents 0, 1or 2), a halogen atom or a hydrogen atom, andn represents 0, 1 or 2,or an N-oxide thereof.

A compound represented by the formula (1-2):

whereinA^(3b) represents a nitrogen atom or ═CR^(9b) (wherein R^(9b) representsa hydrogen atom or a halogen atom),R^(1b) represents an ethyl group or a cyclopropylmethyl group,R^(7b) represents methyl group or a propargyl group,R^(3b) represents a C1-C6 alkyl group optionally substituted by one ormore halogen atoms, —OR^(20b) (wherein R^(20b) represents a C1-C6 alkylgroup optionally substituted by one or more halogen atoms),—S(O)_(m)R^(20b) (wherein R^(20b) represents a C1-C6 alkyl groupoptionally substituted by one or more halogen atoms, m represents 0, 1or 2), a halogen atom or a hydrogen atom,R^(5b) represents a C1-C6 haloalkyl group, —OR^(22b) (wherein R^(22b)represents a C1-C6 haloalkyl group), —S(O)_(m)R^(23b) (wherein R^(23b)represents a C1-C6 haloalkyl group, m represents 0, 1 or 2), —SF₅ or ahalogen atom, andn represents 0, 1 or 2,or an N-oxide thereof.

A compound represented by the formula (1-3):

whereinA^(3b) represents a nitrogen atom or ═CR^(9b)— (wherein R^(9b)represents a hydrogen atom or a halogen atom),R^(1b) represents an ethyl group or a cyclopropylmethyl group,R^(3b) represents a C1-C6 alkyl group optionally substituted by one ormore halogen atoms, —OR^(2b) (wherein R^(20b) represents a C1-C6 alkylgroup optionally substituted by one or more halogen atoms),—S(O)_(m)R^(21b) (wherein R^(21b) represents a C1-C6 alkyl groupoptionally substituted by one or more halogen atoms, m represents 0, 1or 2), a halogen atom or a hydrogen atom,R^(5b) represents a C1-C6 haloalkyl group, —OR^(22b) (wherein R^(22b)represents a C1-C6 haloalkyl group), —S(OR^(23b) (wherein R^(23b)represents a C1-C6 haloalkyl group, m represents 0, 1 or 2), —SF₅ or ahalogen atom, andn represents 0, 1 or 2,or an N-oxide thereof.

A compound represented by the formula (1-4):

whereinA^(3b) represents a nitrogen atom or ═CR^(9b)— (wherein R^(9b)represents a hydrogen atom or a halogen atom),R^(1b) represents an ethyl group or a cyclopropylmethyl group,R^(3b) represents a C1-C6 alkyl group optionally substituted by one ormore halogen atoms, —OR^(20b) (wherein R^(20b) represents a C1-C6 alkylgroup optionally substituted by one or more halogen atoms),—S(O)_(m)R^(21b) (wherein R^(21b) represents a C1-C6 alkyl groupoptionally substituted by one or more halogen atoms, m represents 0, 1or 2), a halogen atom or a hydrogen atom,R^(5b) represents a C1-C6 haloalkyl group, OR^(22b) (wherein R^(22b)represents a C1-C6 haloalkyl group), —S(O)_(m)R^(23b) (wherein R^(23b)represents a C1-C6 haloalkyl group, m represents 0, 1 or 2), —SF₅ or ahalogen atom, andn represents 0, 1 or 2,or an N-oxide thereof.

A compound represented by the formula (1-5):

whereinR^(70a) represents a hydrogen atom or a C2-C6 alkoxyalkyl groupoptionally substituted by one or more halogen atoms,A^(3a) represents a nitrogen atom or ═CR^(9a)—,R^(1a) represents a C1-C6 alkyl group optionally substituted by one ormore atoms: or groups selected from the group consisting of a halogenatom and a cyclopropyl group (wherein the cyclopropyl group isoptionally substituted by one or more halogen atoms or one or more C1-C3alkyl groups), a C2-C6 alkenyl group optionally substituted by one ormore halogen atoms or a C2-C6 alkynyl group optionally substituted byone or more halogen atoms,R^(2a) and R^(4a) are the same or different and each represents ahalogen atom or a hydrogen atom,R^(3a) represents a C1-C6 alkyl group optionally substituted by one ormore halogen atoms, a C2-C6 alkenyl group optionally substituted by oneor more halogen atoms, a C2-C6 alkynyl group optionally substituted byone or more halogen atoms, 5- or 6-membered aromatic heterocyclic group(wherein the 5- or 6-membered aromatic heterocyclic group is optionallysubstituted by one or more atoms or substituents selected from the groupconsisting of a halogen atom, a C1-C3 alkyl group optionally substitutedby one or more halogen atoms, and a C1-C3 alkoxy group optionallysubstituted by one or more halogen atoms), —OR^(20a) (wherein R^(20a)represents a C1-C6 alkyl group optionally substituted by one or morehalogen atoms), —S(O)_(m)R^(21a) (wherein R^(21a) represents a C1-C6alkyl group optionally substituted by one or more halogen atoms, mrepresents 0, 1 or 2), a cyano group, a nitro group, a halogen atom or ahydrogen atom,R^(5a) represents a C1-C6 alkyl group optionally substituted by one ormore halogen atoms, —OR^(22a) (wherein R^(22a) represents a C1-C6 alkylgroup optionally substituted by one or more halogen atoms),—S(O)_(m)R^(23a) (wherein R^(23a) represents a C1-C6 alkyl groupoptionally substituted by one or more halogen atoms, m represents 0, 1or 2), —SF₅ or a halogen atom,R^(9a) represents a C1-C6 alkyl group optionally substituted by one ormore halogen atoms, —OR^(24a) (wherein R^(24a) represents a C1-C6 alkylgroup optionally substituted by one or more halogen atoms),—S(O)_(m)R^(25a) (wherein R^(25a) represents a C1-C6 alkyl groupoptionally substituted by one or more halogen atoms, m represents 0, 1or 2), a halogen atom or a hydrogen atom, andn represents 0, 1 or 2,or an N-oxide thereof.

A compound represented by the formula (1-5) wherein

R^(70a) is a hydrogen atom or a C2-C6 alkoxyalkyl group,A^(3a) is a nitrogen atom or ═CR^(9a)—,R^(1a) is a C1-C6 alkyl group optionally substituted by one or moreatoms or groups selected from the group consisting of a halogen atom anda cyclopropyl group (wherein the cyclopropyl group is optionallysubstituted by one or more halogen atoms or one or more C1-C3 alkylgroups), a C2-C6 alkenyl group optionally substituted by one or morehalogen atoms or a C2-C6 alkynyl group optionally substituted by one ormore halogen atoms,R^(2a) and R^(4a) are the same or different and each represents ahalogen atom or a hydrogen atom,R^(3a) is a C1-C6 alkyl group optionally substituted by one or morehalogen atoms, a C2-C6 alkenyl group optionally substituted by one ormore halogen atoms, a C2-C6 alkynyl group optionally substituted by oneor more halogen atoms, 5- or 6-membered aromatic heterocyclic group(wherein the 5- or 6-membered aromatic heterocyclic group is optionallysubstituted by one or more atoms or groups selected from the groupconsisting of a halogen atom, a C1-C3 alkyl group optionally substitutedby one or more halogen atoms, and a C1-C3 alkoxy group optionallysubstituted by one or more halogen atoms), —OR^(20a) (wherein R^(20a)represents a C1-C6 alkyl group optionally substituted by one or morehalogen atoms), —S(O)_(m)R^(21a) (wherein R^(21a) represents a C1-C6alkyl group optionally substituted by one or more halogen atoms, mrepresents 0, 1 or 2), a cyano group, a nitro group, a halogen atom or ahydrogen atom,R^(5a) is a C1-C6 alkyl group optionally substituted by one or morehalogen atoms, —OR^(22a) (wherein R^(22a) represents a C1-C6 alkyl groupoptionally substituted by one or more halogen atoms), —S(O)_(m)R^(23a)(wherein R^(23a) represents a C1-C6 alkyl group optionally substitutedby one or more halogen atoms, m represents 0, 1 or 2), —SF₅ or a halogenatom,R^(9a) is a C1-C6 alkyl group optionally substituted by one or morehalogen atoms, —OR^(24a) (wherein R^(24a) represents a C1-C6 alkyl groupoptionally substituted by one or more halogen atoms), —S(O)_(m)R^(25a)(wherein R^(25a) represents a C1-C6 alkyl group optionally substitutedby one or more halogen atoms, m represents 0, 1 or 2), a halogen atom ora hydrogen atom, andn is 0, 1 or 2,or an N-oxide thereof.

A compound represented by the formula (1-6):

whereinR^(70b) represents a hydrogen atom or a C2-C6 alkoxyalkyl groupoptionally substituted by one or more halogen atoms,A^(3b) represents a nitrogen atom or ═CR^(9b)— (wherein R^(9b)represents a hydrogen atom or a halogen atom),R^(1b) represents an ethyl group or a cyclopropylmethyl group,R^(3b) represents a C1-C6 alkyl group optionally substituted by one ormore halogen atoms, —OR^(2b) (wherein R^(20b) represents a C1-C6 alkylgroup optionally substituted by one or more halogen atoms),—S(O)_(m)R^(21b) (wherein R^(21b) represents a C1-C6 alkyl groupoptionally substituted by one or more halogen atoms, m represents 0, 1or 2), a halogen atom or a hydrogen atom,R^(5b) represents a C1-C6 haloalkyl group, —OR^(22b) (wherein R^(22b)represents a C1-C6 haloalkyl group), —S(O)_(m)R^(23b) (wherein R^(23b)represents a C1-C6 haloalkyl group, m represents 0, 1 or 2), —SF₅ or ahalogen atom, andn represents 0, 1 or 2,or an N-oxide thereof.

A compound represented by the formula (1):

A compound represented by the formula (1) wherein A¹ is —NR⁷—;

A compound represented by the formula (1) wherein A¹ is an oxygen atom;

A compound represented by the formula (1) wherein A¹ is a sulfur atom;

A compound represented by the formula (1) wherein A² is ═CR⁸—;

A compound represented by the formula (1) wherein A² is ═CR⁸—, and A³ isa nitrogen atom;

A compound represented by the formula (1) wherein A² is ═CR⁸—, and A³ is═CR⁹—;

A compound represented by the formula (1) wherein A¹ is —NR⁷—, and A² is═CR⁸—;

A compound represented by the formula (1) wherein A¹ is —NR⁷—, A² is═CR⁸—, and A³ is a nitrogen atom;

A compound represented by the formula (1) wherein A¹ is —NR⁷—, A² is═CR⁸—, and A³ is ═CR⁹—;

A compound represented by the formula (1) wherein A¹ is an oxygen atom,and A² is ═CR⁸—;

A compound represented by the formula (1) wherein A¹ is an oxygen atom,A² is ═CR⁸—, and A³ is a nitrogen atom;

A compound represented by the formula (1) wherein A¹ is an oxygen atom,A² is ═CR⁸—, and A³ is ═CR⁹—;

A compound represented by the formula (1) wherein A¹ is a sulfur atom,and A² is ═CR⁸—;

A compound represented by the formula (1) wherein A¹ is a sulfur atom,A² is ═CR⁸—, and A³ is a nitrogen atom;

A compound represented by the formula (1) wherein A¹ is a sulfur atom,A² is ═CR⁸—, and A³ is ═CR⁹—;

A compound represented by the formula (1) wherein R¹ is a C1-C6 chainhydrocarbon group optionally substituted by one or more atoms or groupsselected from Group X;

A compound represented by the formula (1) wherein R¹ is a C1-C6 alkylgroup optionally substituted by one or more atoms or groups selectedfrom the group consisting of a halogen atom and a cyclopropyl group(wherein the cyclopropyl group is optionally substituted by one or morehalogen atoms or one or more C1-C3 alkyl groups), a C2-C6 alkenyl groupoptionally substituted by one or more halogen atoms or a C2-C6 alkynylgroup optionally substituted by one or more halogen atoms;

A compound represented by the formula (1) wherein R³ is a C1-C6 chainhydrocarbon group optionally substituted by one or more atoms or groupsselected from Group X, a phenyl group optionally substituted by one ormore atoms or groups selected from Group Z, a 5-membered heterocyclicgroup optionally substituted by one or more atoms or groups selectedfrom Group Z, a 6-membered heterocyclic group optionally substituted byone or more atoms or groups selected from Group Z, —OR¹⁰, —S(O)_(m)R¹⁰,—SF₅, a cyano group, a nitro group, a halogen atom or a hydrogen atom;

A compound represented by the formula (1) wherein R³ is a C1-C6 alkylgroup optionally substituted by one or more halogen atoms, a C2-C6alkenyl group optionally substituted by one or more halogen atoms, aC2-C6 alkynyl group optionally substituted by one or more halogen atoms,5-membered aromatic heterocyclic group (wherein the aromaticheterocyclic group is optionally substituted by one or more atoms orsubstituents selected from the group consisting of a halogen atom, aC1-C3 alkyl group optionally substituted by one or more halogen atoms,and a C1-C3 alkoxy group optionally substituted by one or more halogenatoms), 6-membered aromatic heterocyclic group (wherein the aromaticheterocyclic group is optionally substituted by one or more atoms orsubstituents selected from the group consisting of a halogen atom, aC1-C3 alkyl group optionally substituted by one or more halogen atoms,and a C1-C3 alkoxy group optionally substituted by one or more halogenatoms), —OR¹⁰ (wherein R¹⁰ is a C1-C6 alkyl group optionally substitutedby one or more halogen atoms), —S(O)_(m)R¹⁰ (wherein R¹⁰ is a C1-C6alkyl group optionally substituted by one or more halogen atoms), acyano group, a nitro group, a halogen atom or a hydrogen atom;

A compound represented by the formula (1) wherein R² and R⁴ are the sameor different each other and each represents a C1-C6 chain hydrocarbongroup optionally substituted by one or more atoms or groups selectedfrom Group X, a phenyl group optionally substituted by one or more atomsor groups selected from Group Z, a 5-membered heterocyclic groupoptionally substituted by one or more atoms or groups selected fromGroup Z, a 6-membered heterocyclic group optionally substituted by oneor more atoms or groups selected from Group Z, —OR¹⁰, —S(O)_(m)R¹⁰,—SF₅, a cyano group, a nitro group, a halogen atom or a hydrogen atom;

A compound represented by the formula (1) wherein R² and R⁴ are the sameor different each other and each represents a halogen atom or a hydrogenatom;

A compound represented by the formula (1) wherein R⁵ is a C1-C6 chainhydrocarbon group optionally substituted by one or more atoms or groupsselected from Group X, —OR¹⁰, —S(O)_(m)R¹⁰, —SF₅, a halogen atom or ahydrogen atom;

A compound represented by the formula (1) wherein R⁵ is a C1-C6 chainhydrocarbon group optionally substituted by one or more atoms or groupsselected from Group X, —OR¹⁰, —S(O)_(m)R¹⁰, —SF₅ or a halogen atom;

A compound represented by the formula (1) wherein R⁵ is a C1-C6 alkylgroup optionally substituted by one or more halogen atoms, —OR¹⁰(wherein R¹⁰ is a C1-C6 alkyl group optionally substituted by one ormore halogen atoms), —S(O)_(m)R¹⁰ (wherein R¹⁰ is a C1-C6 alkyl groupoptionally substituted by one or more halogen atoms), —SF₅ or a halogenatom;

A compound represented by the formula (1) wherein when A¹ is —NR⁷—, R⁷is a C1-C6 chain hydrocarbon group optionally substituted by one or moreatoms or groups selected from Group W, a C1-C6 chain hydrocarbon groupsubstituted by one phenyl group (wherein the phenyl group is optionallysubstituted by one or more atoms or groups selected from Group Z), aC1-C6 chain hydrocarbon group substituted by one 5-membered heterocyclicgroup (wherein the 5-membered heterocyclic group is optionallysubstituted by one or more atoms or groups selected from Group Z), aC1-C6 chain hydrocarbon group substituted by one 6-membered heterocyclicgroup (wherein the 6-membered heterocyclic group is optionallysubstituted by one or more atoms or groups selected from Group Z) or ahydrogen atom;

A compound represented by the formula (1) wherein when A¹ is —NR⁷—, R⁷is a C1-C6 alkyl group optionally substituted by one or more halogenatoms, a C3-C6 alkenyl group optionally substituted by one or morehalogen atoms, a C3-C6 alkynyl group optionally substituted by one ormore halogen atoms, a C1-C6 alkyl group substituted by one 5-memberedaromatic heterocyclic group (wherein the 5-membered aromaticheterocyclic group is optionally substituted by one or more atoms orsubstituents selected from the group consisting of a halogen atom, aC1-C3 alkyl group optionally substituted by one or more halogen atoms,and a C1-C3 alkoxy group optionally substituted by one or more halogenatoms), a C1-C6 alkyl group substituted by one 6-membered aromaticheterocyclic group (wherein the 6-membered aromatic heterocyclic groupis optionally substituted by one or more atoms or substituents selectedfrom the group consisting of a halogen atom, a C1-C3 alkyl groupoptionally substituted by one or more halogen atoms, and a C1-C3 alkoxygroup optionally substituted by one or more halogen atoms), a hydrogenatom or a C2-C6 alkoxyalkyl group;

A compound represented by the formula (1) wherein when A¹ is —NR⁷—, R⁷is a C1-C6 alkyl group optionally substituted by one or more halogenatoms, a C3-C6 alkenyl group optionally substituted by one or morehalogen atoms, a C3-C6 alkynyl group optionally substituted by one ormore halogen atoms; a C1-C6 alkyl group substituted by one 5-memberedaromatic heterocyclic group (wherein the 5-membered aromaticheterocyclic group is optionally substituted by one or more atoms orsubstituents selected from the group consisting of a halogen atom, aC1-C3 alkyl group optionally substituted by one or more halogen atoms,and a C1-C3 alkoxy group optionally substituted by one or more halogenatoms) or a C1-C6 alkyl group substituted by one 6-membered aromaticheterocyclic group (wherein the 6-membered aromatic heterocyclic groupis optionally substituted by one or more atoms or substituents selectedfrom the group consisting of a halogen atom, a C1-C3 alkyl groupoptionally substituted by one or more halogen atoms, and a C1-C3 alkoxygroup optionally substituted by one or more halogen atoms);

A compound represented by the formula (1) wherein when A¹ is —NR⁷—, R⁷is a C1-C6 alkyl group optionally substituted by one or more halogenatoms, a C3-C6 alkenyl group optionally substituted by one or morehalogen atoms, a C3-C6 alkynyl group optionally substituted by one ormore halogen atoms, a C1-C6 alkyl group substituted by one thiazolylgroup (wherein the thiazolyl group is optionally substituted by one ormore atoms or substituents selected from the group consisting of ahalogen atom, a C1-C3 alkyl group optionally substituted by one or morehalogen atoms, and a C1-C3 alkoxy group optionally substituted by one ormore halogen atoms), a C1-C6 alkyl group substituted by one pyridylgroup (wherein the pyridyl group is optionally substituted by one ormore atoms or substituents selected from the group consisting of ahalogen atom, a C1-C3 alkyl group optionally substituted by one or morehalogen atoms, and a C1-C3 alkoxy group optionally substituted by one ormore halogen atoms), a hydrogen atom or a C2-C6 alkoxyalkyl group;

A compound represented by the formula (1) wherein when A¹ is —NR⁷—, R⁷is a methyl group, an ethyl group, a propyl group, an allyl group, apropargyl group, a (2-chlorothiazol-5-yl)methyl group, a(2-chloropyridin-5-yl)methyl group, a hydrogen atom, a methoxymethylgroup, an ethoxymethyl group, a 1-(methoxy)ethyl group or a1-(ethoxy)ethyl group;

A compound represented by the formula (1) wherein A¹ is —NR⁷—, and R⁷ isa hydrogen atom or a C2-C6 alkoxyalkyl group;

A compound represented by the formula (1) wherein A¹ is —NR⁷—, and R⁷ isa hydrogen atom, a methoxymethyl group, an ethoxymethyl group, a1-(methoxy)ethyl group or a 1-(ethoxy)ethyl group;

A compound represented by the formula (1) wherein when A² is ═CR⁸—, R⁸is a C1-C6 chain hydrocarbon group optionally substituted by one or morehalogen atoms, —OR¹⁰, —S(O)_(m)R¹⁰, a halogen atom or a hydrogen atom;

A compound represented by the formula (1) wherein when A² is ═CR⁸—, R⁸is a C1-C6 alkyl group optionally substituted by one or more halogenatoms, —OR¹⁰ (wherein R¹⁰ is a C1-C6 alkyl group optionally substitutedby one or more halogen atoms), —S(O)_(m)R¹⁰ (wherein R¹⁰ is a C1-C6alkyl group optionally substituted by one or more halogen atoms), ahalogen atom or a hydrogen atom;

A compound represented by the formula (1) wherein when A² is ═CR⁸—, R⁸is a halogen atom or a hydrogen atom;

A compound represented by the formula (1) wherein when A² is ═CR⁸—, R⁸is a hydrogen atom;

A compound represented by the formula (1) wherein when A³ is ═CR⁹—, R⁹is a C1-C6 chain hydrocarbon group optionally substituted by one or morehalogen atoms, a halogen atom or a hydrogen atom;

A compound represented by the formula (1) wherein when A³ is ═CR⁹—, R⁹is a C1-C6 alkyl group optionally substituted by one or more halogenatoms, —OR¹⁰ (wherein R¹⁰ is a C1-C6 alkyl group optionally substitutedby one or more halogen atoms), —S(O)_(m)R¹⁰ (wherein R¹⁰ is a C1-C6alkyl group optionally substituted by one or more halogen atoms), ahalogen atom or a hydrogen atom;

A compound represented by the formula (1) wherein R¹ is a C1-C6 alkylgroup optionally substituted by one or more atoms or groups selectedfrom the group consisting of a halogen atom and a cyclopropyl group(wherein the cyclopropyl group is optionally substituted by one or morehalogen atoms or one or more C1-C3 alkyl groups);

A compound represented by the formula (1) wherein R¹ is a C1-C6 alkylgroup, a C1-C6 haloalkyl group, or a C4-C9 cyclopropylalkyl group(wherein the cyclopropyl group is optionally substituted by one or morehalogen atoms or one or more C1-C3 alkyl groups);

A compound represented by the formula (1) wherein R¹ is a C2-C6 alkylgroup, a C1-C6 haloalkyl group or C4-C9 cyclopropylalkyl group (whereinthe cyclopropyl group is optionally substituted by one or more halogenatoms or one or more C1-C3 alkyl groups);

A compound represented by the formula (1) wherein R¹ is a methyl group,an ethyl group, a propyl group, an isopropyl group, a trifluoromethylgroup, a 2,2,2-trifluoroethyl group or a cyclopropylmethyl group;

A compound represented by the formula (1) wherein R¹ is an ethyl groupor a cyclopropylmethyl group;

A compound represented by the formula (1) wherein R¹ is an ethyl group;

A compound represented by the formula (1) wherein R³ is a C1-C6 alkylgroup optionally substituted by one or more halogen atoms, a C2-C6alkenyl group optionally substituted by one or more halogen atoms, aC2-CG alkynyl group optionally substituted by one or more halogen atoms,pyridyl group (wherein the pyridyl group is optionally substituted byone or more atoms or substituents selected from the group consisting ofa halogen atom, a C1-C3 alkyl group optionally substituted by one ormore halogen atoms, and a C1-C3 alkoxy group optionally substituted byone or more halogen atoms), a pyrimidinyl group (wherein the pyrimidinylgroup is optionally substituted by one or more atoms or substituentsselected from the group consisting of a halogen atom, a C1-C3 alkylgroup optionally substituted by one or more halogen atoms, and a C1-C3alkoxy group optionally substituted by one or more halogen atoms),—OR^(20a) (wherein R^(20a) is a C1-C6 alkyl group optionally substitutedby one or more halogen atoms), —S(O)_(m)R^(21a) (wherein R^(21a) is aC1-C6 alkyl group optionally substituted by one or more halogen atoms,and m is 0, 1 or 2), a halogen atom or a hydrogen atom;

A compound represented by the formula (1) wherein R³ is a C1-C6 alkylgroup optionally substituted by one or more halogen atoms, —OR^(2b)(wherein R^(20b) represents a C1-C6 alkyl group optionally substitutedby one or more halogen atoms), —S(O)_(m)R^(21b) (wherein R^(21b)represents a C1-C6 alkyl group optionally substituted by one or morehalogen atoms, m represents 0, 1 or 2), a halogen atom or a hydrogenatom;

A compound represented by the formula (1) wherein R³ is a methyl group,a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group,an ethyl group, an ethenyl group, an ethynyl group, a fluoromethylgroup, a difluoromethyl group, a trifluoromethyl group, —CF₂CF₃,—CF₂CF₂CF₃, —CF(CF₃)₂, —CF₂CF₂CF₂CF₃, —OCF₃, —OCF₂CF₃, —SCF₃, —S(O)CF₃,—S(O)₂CF₃, —SCF₂CF₃, —S(O)CF₂CF₃, —S(O)₂CF₂CF₃, a 2-pyridyl group, a5-trifluoromethyl-2-pyridyl group, a 2-pyrimidinyl group, a fluorineatom, a chlorine atom, a bromine atom, an iodine atom or a hydrogenatom;

A compound represented by the formula (1) wherein R³ is a methyl group,a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group,an ethyl group, an ethenyl group, an ethynyl group, a fluoromethylgroup, a difluoromethyl group, a trifluoromethyl group, —CF₂CF₃,—CF₂CF₂CF₃, —CF(CF₃)₂, —CF₂CF₂CF₂CF₃, —OCF₃, —OCF₂CF₃, —SCF₃, —S(O)CF₃,—S(O)₂CF₃, —SCF₂CF₃, —S(O)CF₂CF₃, —S(O)₂CF₂CF₃, a fluorine atom, achlorine atom, a bromine atom, an iodine atom or a hydrogen atom;

A compound represented by the formula (1) wherein R² and R⁴ both are ahydrogen atom;

A compound represented by the formula (1) wherein R⁵ is a C1-C6haloalkyl group, —OR^(22b) (wherein R^(22b) is a C1-C6 haloalkyl group),—S(O)_(m)R^(23b) (wherein R^(23b) is a C1-C6 haloalkyl group, and m is0, 1 or 2), —SF₅ or a halogen atom;

A compound represented by the formula (1) wherein R⁵ is a C1-C6haloalkyl group, —OR^(22b) (wherein R^(22b) is a C1-C6 haloalkyl group),—S(O)_(m)R^(23b) (wherein R^(23b) is a C1-C6 haloalkyl group, and m is0, 1 or 2) or —SF₅;

A compound represented by the formula (1) wherein R⁵ is a C1-C6haloalkyl group, —OR^(22b) (wherein R^(22b) is a C1-C6 haloalkyl group),—S(O)_(m)R^(23b) (wherein R^(23b) is a C1-C6 haloalkyl group, and m is0, 1 or 2) or a halogen atom;

A compound represented by the formula (1) wherein R⁵ is a C1-C6haloalkyl group, —OR^(22b) (wherein R^(22b) is a C1-C6 haloalkyl group)or —S(O)_(m)R^(23b) (wherein R^(23b) is a C1-C6 haloalkyl group, and mis 0, 1 or 2);

A compound represented by the formula (1) wherein R⁵ is a C1-C6perfluoroalkyl group, —OR¹⁰ (wherein R¹⁰ is a C1-C6 perfluoroalkylgroup) or —S(O)_(m)R¹⁰ (wherein R¹⁰ is a C1-C6 perfluoroalkyl group);

A compound represented by the formula (1) wherein R⁵ is atrifluoromethyl group, —CF₂CF₃, —CF₂C₂CF₃, —CF(CF₃)₂, —OCF₃, —OCF₂CF₃,—SCF₃, —S(O)CF₃, —S(O)₂CF₃, —SCF₂CF₃, —S(O)CF₂CF₃, —S(O)₂CF₂CF₃, SF₅, afluorine atom, a chlorine atom, a bromine atom or an iodine atom;

A compound represented by the formula (1) wherein when A¹ is —NR⁷—, R⁷is a C1-C6 alkyl group optionally substituted by one or more halogenatoms, a C3-C6 alkenyl group optionally substituted by one or morehalogen atoms, a C3-C6 alkynyl group optionally substituted by one ormore halogen atoms, a C1-C6 alkyl group substituted by one thiazolylgroup (wherein the thiazolyl group is optionally substituted by one ormore atoms or substituents selected from the group consisting of ahalogen atom, a C1-C3 alkyl group optionally substituted by one or morehalogen atoms, and a C1-C3 alkoxy group optionally substituted by one ormore halogen atoms) or a C1-C6 alkyl group substituted by one pyridylgroup (wherein the pyridyl group is optionally substituted by one ormore atoms or substituents selected from the group consisting of ahalogen atom, a C1-C3 alkyl group optionally substituted by one or morehalogen atoms, and a C1-C3 alkoxy group optionally substituted by one ormore halogen atoms);

A compound represented by the formula (1) wherein when A¹ is —NR⁷—, R⁷is a methyl group, an ethyl group, a propyl group, an allyl group, apropargyl group, (2-chlorothiazol-5-yl)methyl group, or,(2-chloropyridin-5-yl)methyl group;

A compound represented by the formula (1) wherein when A¹ is —NR⁷—, R⁷is a methyl group or a propargyl group;

A compound represented by the formula (1) wherein when A³ is ═CR⁹—, R⁹is a halogen atom or a hydrogen atom;

A compound represented by the formula (1) wherein when A³ is ═CR⁹—, R⁹is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or ahydrogen atom;

A compound represented by the formula (1) wherein when A³ is ═CR⁹—, R⁹is a fluorine atom or a hydrogen atom;

A compound represented by the formula (1) wherein R¹ is a C1-C6 chainhydrocarbon group optionally substituted by one or more atoms or groupsselected from Group X,

R², R³ and R⁴ are the same or different each other and each represents aC1-C6 chain hydrocarbon group optionally substituted by one or moreatoms or groups selected from Group X, a phenyl group optionallysubstituted by one or more atoms or groups selected from Group Z, a5-membered heterocyclic group optionally substituted by one or moreatoms or groups selected from Group Z, a 6-membered heterocyclic groupoptionally substituted by one or more atoms or groups selected fromGroup Z, —OR¹⁰, —S(O)_(m)R¹⁰, —SF₅, a cyano group, a nitro group, ahalogen atom or a hydrogen atom,R⁵ and R⁶ are the same or different each other and each represents aC1-C6 chain hydrocarbon group optionally substituted by one or moreatoms or groups selected from Group X, —OR¹⁰, —S(O)_(m)R¹⁰, —SF₅, ahalogen atom or a hydrogen atom,when A¹ is —NR⁷—, R⁷ is a C1-C6 chain hydrocarbon group optionallysubstituted by one or more atoms or groups selected from Group W, aC1-C6 chain hydrocarbon group substituted by one phenyl group (whereinthe phenyl group is optionally substituted by one or more atoms orgroups selected from Group Z), a C1-C6 chain hydrocarbon groupsubstituted by one 5-membered heterocyclic group (wherein the 5-memberedheterocyclic group is optionally substituted by one or more atoms orgroups selected from Group Z), a C1-C6 chain hydrocarbon groupsubstituted by one 6-membered heterocyclic group (wherein the 6-memberedheterocyclic group is optionally substituted by one or more atoms orgroups selected from Group Z) or a hydrogen atom, when A² is ═CR⁸—, R⁸is a C1-C6 chain hydrocarbon group optionally substituted by one or morehalogen atoms, —OR¹⁰, —S(O)_(m)R¹⁰, a halogen atom or a hydrogen atom,when A³ is ═CR⁹—, R⁹ is a C1-C6 chain hydrocarbon group optionallysubstituted by one or more halogen atoms, —OR¹⁰, —S(O)_(m)R¹⁰, a halogenatom or a hydrogen atom.

A compound represented by the formula (1) wherein R¹ is a C1-C6 alkylgroup optionally substituted by one or more atoms or groups selectedfrom the group consisting of a halogen atom and a cyclopropyl group(wherein the cyclopropyl group is optionally substituted by one or morehalogen atoms or one or more C1-C3 alkyl groups), a C2-C6 alkenyl groupoptionally substituted by one or more halogen atoms or a C2-C6 alkynylgroup optionally substituted by one or more halogen atoms,

R² and R⁴ are the same or different each other and each represents ahalogen atom or a hydrogen atom,R³ is a C1-C6 alkyl group optionally substituted by one or more halogenatoms, a C2-C6 alkenyl group optionally substituted by one or morehalogen atoms, a C2-C6 alkynyl group optionally substituted by one ormore halogen atoms, 5-membered aromatic heterocyclic group (wherein thearomatic heterocyclic group is optionally substituted by one or moreatoms or substituents selected from the group consisting of a halogenatom, a C1-C3 alkyl group optionally substituted by one or more halogenatoms, and a C1-C3 alkoxy group optionally substituted by one or morehalogen atoms), 6-membered aromatic heterocyclic group (wherein thearomatic heterocyclic group is optionally substituted by one or moreatoms or substituents selected from the group consisting of a halogenatom, a C1-C3 alkyl group optionally substituted by one or more halogenatoms, and a C1-C3 alkoxy group optionally substituted by one or morehalogen atoms), —OR¹⁰, —S(O)_(m)R¹⁰, a cyano group, a nitro group, ahalogen atom or a hydrogen atom,R⁵ is a C1-C6 alkyl group optionally substituted by one or more halogenatoms, —OR¹⁰, —S(O)_(m)R¹⁰, —SF₅ or a halogen atom,R⁶ is a C1-C6 alkyl group optionally substituted by one or more halogenatoms, —OR¹⁰, —S(O)_(m)R¹⁰, a halogen atom or a hydrogen atom,R¹⁰ is a C1-C6 alkyl group optionally substituted by one or more halogenatoms,when A¹ is —NR⁷—, R⁷ is a C1-C6 alkyl group optionally substituted byone or more halogen atoms, a C3-C6 alkenyl group optionally substitutedby one or more halogen atoms, a C3-C6 alkynyl group optionallysubstituted by one or more halogen atoms, a C1-C6 alkyl groupsubstituted by one 5-membered aromatic heterocyclic group (wherein the5-membered aromatic heterocyclic group is optionally substituted by oneor more atoms or substituents selected from the group consisting of ahalogen atom, a C1-C3 alkyl group optionally substituted by one or morehalogen atoms, and a C1-C3 alkoxy group optionally substituted by one ormore halogen atoms), a C1-C6 alkyl group substituted by one 6-memberedaromatic heterocyclic group (wherein the 6-membered aromaticheterocyclic group is optionally substituted by one or more atoms orsubstituents selected from the group consisting of a halogen atom, aC1-C3 alkyl group optionally substituted by one or more halogen atoms,and a C1-C3 alkoxy group optionally substituted by one or more halogenatoms), a hydrogen atom or a C2-C6 alkoxyalkyl group,when A² is ═CR⁸—, R⁸ is a C1-C6 alkyl group optionally substituted byone or more halogen atoms, —OR¹⁰, —S(O)_(m)R¹⁰, a halogen atom or ahydrogen atom,when A³ is ═CR⁹—, R⁹ is a C1-C6 alkyl group optionally substituted byone or more halogen atoms, —OR¹⁰, —S(O)_(m)R¹⁰, a halogen atom or ahydrogen atom.

A compound represented by the formula (1-1) wherein A^(1a) is —NR^(7a)—;

A compound represented by the formula (1-1) wherein A^(1a) is an oxygenatom;

A compound represented by the formula (1-1) wherein A^(1a) is a sulfuratom;

A compound represented by the formula (1-1) wherein A^(1a) is —NR^(7a)—,and A^(3a) is a nitrogen atom;

A compound represented by the formula (1-1) wherein A^(1a) is —NR^(7a),and A^(3a) is ═CR^(9a)— compound;

A compound represented by the formula (1-1) wherein A^(1a) is an oxygenatom, and A^(3a) is a nitrogen atom;

A compound represented by the formula (1-1) wherein A^(1a) is an oxygenatom, and A^(3a) is ═CR^(9a)— compound;

A compound represented by the formula (1-1) wherein A^(1a) is a sulfuratom, and A^(3a) is a nitrogen atom;

A compound represented by the formula (1-1) wherein A^(1a) is a sulfuratom, and A^(3a) is ═CR^(9a)— compound;

A compound represented by the formula (1-1) wherein R^(1a) is a C1-C6alkyl group optionally substituted by one or more atoms or groupsselected from the group consisting of a halogen atom and a cyclopropylgroup (wherein the cyclopropyl group is optionally substituted by one ormore halogen atoms or one or more C1-C3 alkyl groups);

A compound represented by the formula (1-1) wherein R^(1a) is a C1-C6alkyl group, a C1-C6 haloalkyl group, or a C4-C9 cyclopropylalkyl group(wherein the cyclopropyl group is optionally substituted by one or morehalogen atoms or one or more C1-C3 alkyl groups);

A compound represented by the formula (1-1) wherein R^(1a) is a C2-C6alkyl group, a C1-C6 haloalkyl group or C4-C9 cyclopropylalkyl group(wherein the cyclopropyl group is optionally substituted by one or morehalogen atoms or one or more C1-C3 alkyl groups);

A compound represented by the formula (1-1) wherein R^(1a) is a methylgroup, an ethyl group, a propyl group, an isopropyl group, atrifluoromethyl group, a 2,2,2-trifluoroethyl group or acyclopropylmethyl group;

A compound represented by the formula (1-1) wherein R^(1a) is an ethylgroup or a cyclopropylmethyl group;

A compound represented by the formula (1-1) wherein R^(1a) is an ethylgroup;

A compound represented by the formula (1-1) wherein R^(3a) is a C1-C6alkyl group optionally substituted by one or more halogen atoms, a C2-C6alkenyl group optionally substituted by one or more halogen atoms, aC2-C6 alkynyl group optionally substituted by one or more halogen atoms,pyridyl group (wherein the pyridyl group is optionally substituted byone or more atoms or substituents selected from the group consisting ofa halogen atom, a C1-C3 alkyl group optionally substituted by one ormore halogen atoms, and a C1-C3 alkoxy group optionally substituted byone or more halogen atoms), a pyrimidinyl group (wherein the pyrimidinylgroup is optionally substituted by one or more atoms or substituentsselected from the group consisting of a halogen atom, a C1-C3 alkylgroup optionally substituted by one or more halogen atoms, and a C1-C3alkoxy group optionally substituted by one or more halogen atoms),—OR^(20a) (wherein R^(20a) is a C1-C6 alkyl group optionally substitutedby one or more halogen atoms), —S(O)_(m)R^(21a) (wherein R^(21a) is aC1-C6 alkyl group optionally substituted by one or more halogen atoms,and m is 0, 1 or 2), a halogen atom or a hydrogen atom;

A compound represented by the formula (1-1) wherein R^(3a) is a C1-C6alkyl group optionally substituted by one or more halogen atoms,—OR^(20a) (wherein R^(20a) represents a C1-C6 alkyl group optionallysubstituted by one or more halogen atoms), —S(O)_(m)R^(21a) (whereinR^(21a) represents a C1-C6 alkyl group optionally substituted by one ormore halogen atoms, m represents 0, 1 or 2), a halogen atom or ahydrogen atom;

A compound represented by the formula (1-1) wherein R^(3a) is a methylgroup, a fluoromethyl group, a difluoromethyl group, a trifluoromethylgroup, an ethyl group, an ethenyl group, an ethynyl group, afluoromethyl group, a difluoromethyl group, a trifluoromethyl group,—CF₂CF₃, —CF₂CF₂CF₃, —CF(CF₃)₂, —CF₂CF₂CF₂CF₃, —OCF₃, —OCF₂CF₃, —SCF₃,—S(O)CF₃, —S(O)₂CF₃, —SCF₂CF₃, —S(O)CF₂CF₃, —S(O)₂CF₂CF₃, a 2-pyridylgroup, a 5-trifluoromethyl-2-pyridyl group, a 2-pyrimidinyl group, afluorine atom, a chlorine atom, a bromine atom, an iodine atom or ahydrogen atom;

A compound represented by the formula (1-1) wherein R^(3a) is methylgroup, a fluoromethyl group, a difluoromethyl group, a trifluoromethylgroup, an ethyl group, an ethenyl group, an ethynyl group, afluoromethyl group, a difluoromethyl group, a trifluoromethyl group,—CF₂CF₃, —CF₂CF₂CF₃, —CF(CF₃)₂, —CF₂CF₂CF₂CF₃, —OCF₃, —OCF₂CF₃, —SCF₃,—S(O)CF₃, —S(O)₂CF₃, —SCF₂CF₃, —S(O)CF₂CF₃, —S(O)₂CF₂CF₃, a fluorineatom, a chlorine atom, a bromine atom, an iodine atom or a hydrogenatom;

A compound represented by the formula (1-1) wherein R^(2a) and R^(4a)both are a hydrogen atom;

A compound represented by the formula (1-1) wherein R^(5a) is a C1-C6haloalkyl group, —OR^(22a) (wherein R^(22a) is a C1-C6 haloalkyl group),—S(O)_(m)R^(23a) (wherein R^(23a) is a C1-C6 haloalkyl group, and m is0, 1 or 2), —SF₅ or a halogen atom;

A compound represented by the formula (1-1) wherein R^(5a) is a C1-C6haloalkyl group, —OR^(22a) (wherein R^(22a) is a C1-C6 haloalkyl group),—S(O)_(m)R^(23a) (wherein R^(23a) is a C1-C6 haloalkyl group, and m is0, 1 or 2) or —SF₅;

A compound represented by the formula (1-1) wherein R^(5a) is a C1-C6haloalkyl group, —OR^(22a) (wherein R^(22a) is a C1-C6 haloalkyl group),—S(O)_(m)R^(23a) (wherein R^(23a) is a C1-C6 haloalkyl group, and m is0, 1 or 2) or a halogen atom;

A compound represented by the formula (1-1) wherein R^(5a) is a C1-C6haloalkyl group, —OR^(22a) (wherein R^(22a) is a C1-C6 haloalkyl group)or —S(O)_(m)R^(23a) (wherein R^(23a) is a C1-C6 haloalkyl group, and mis 0, 1 or 2);

A compound represented by the formula (1-1) wherein R^(5a) is a C1-C6perfluoroalkyl group, —OR^(22a) (wherein R^(22a) is a C1-C6perfluoroalkyl group) or —S(O)_(m)R^(23a) (wherein R^(23a) is a C1-C6perfluoroalkyl group);

A compound represented by the formula (1-1) wherein R^(5a) is atrifluoromethyl group, —CF₂CF₃, —CF₂CF₂CF₃, —CF(CF₃)₂, —OCF₃, —OCF₂CF₃,—SCF₃, S(O)CF₃, —S(O)₂CF₃, —SCF₂CF₃, —S(O)CF₂CF₃, —S(O)₂CF₂CF₃, SF₅, afluorine atom, a chlorine atom, a bromine atom or an iodine atom;

A compound represented by the formula (1-1) wherein when A^(1a) is—NR^(7a)—, R^(7a) is a C1-C6 alkyl group optionally substituted by oneor more halogen atoms, a C3-C6 alkenyl group optionally substituted byone or more halogen atoms, a C3-C6 alkynyl group optionally substitutedby one or more halogen atoms, a C1-C6 alkyl group substituted by onethiazolyl group (wherein the thiazolyl group is optionally substitutedby one or more atoms or substituents selected from the group consistingof a halogen atom, a C1-C3 alkyl group optionally substituted by one ormore halogen atoms, and a C1-C3 alkoxy group optionally substituted byone or more halogen atoms) or a C1-C6 alkyl group substituted by onepyridyl group (wherein the pyridyl group is optionally substituted byone or more atoms or substituents selected from the group consisting ofa halogen atom, a C1-C3 alkyl group optionally substituted by one ormore halogen atoms, and a C1-C3 alkoxy group optionally substituted byone or more halogen atoms);

A compound represented by the formula (1-1) wherein when A^(1a) is—NR^(7a)—, R^(7a) is a methyl group, an ethyl group, a propyl group, anallyl group, a propargyl group, (2-chlorothiazol-5-yl)methyl group, or,(2-chloropyridin-5-yl)methyl group;

A compound represented by the formula (1-1) wherein when A^(1a) is—NR^(7a)—, R^(7a) is a methyl group or a propargyl group;

A compound represented by the formula (1-1) wherein when A^(3a) is═CR^(9a)—, R^(9a) is a halogen atom or a hydrogen atom;

A compound represented by the formula (1-1) wherein when A^(3a) is═CR^(9a)—, R^(9a) is a fluorine atom, a chlorine atom, a bromine atom,an iodine atom or a hydrogen atom;

A compound represented by the formula (1-1) wherein when A^(3a) is═CR^(9a)—, R^(9a) is a fluorine atom or a hydrogen atom;

A compound represented by the formula (1-2) wherein A^(3b) is a nitrogenatom;

A compound represented by the formula (1-2) wherein A^(3b) is ═CR^(9b)—compound;

A compound represented by the formula (1-2) wherein R^(1b) is an ethylgroup;

A compound represented by the formula (1-2) wherein R^(3b) is a methylgroup, a fluoromethyl group, a difluoromethyl group, a trifluoromethylgroup, an ethyl group, an ethenyl group, an ethynyl group, afluoromethyl group, a difluoromethyl group, a trifluoromethyl group,—CF₂CF₃, —CF₂CF₂CF₃, —CF(CF₃)₂, —CF₂CF₂CF₂CF₃, —OCF₃, —OCF₂CF₃, —SCF₃,—S(O)CF₃, —S(O)₂CF₃, —SCF₂CF₃, —S(O)CF₂CF₃, —S(O)₂CF₂CF₃, a fluorineatom, a chlorine atom, a bromine atom, an iodine atom or a hydrogenatom;

A compound represented by the formula (1-2) wherein R^(5b) is a C1-C6haloalkyl group, —OR^(22b) (wherein R^(22b) is a C1-C6 haloalkyl group),—S(O)_(m)R^(23b) (wherein R^(23b) is a C1-C6 haloalkyl group, and m is0, 1 or 2), —SF₅ or a halogen atom;

A compound represented by the formula (1-2) wherein R^(5b) is a C1-C6haloalkyl group, —OR^(22b) (wherein R^(22b) is a C1-C6 haloalkyl group),—S(O)_(m)R^(23b) (wherein R^(23b) is a C1-C6 haloalkyl group, and m is0, 1 or 2) or —SF₅;

A compound represented by the formula (1-2) wherein R^(5b) is a C1-C6haloalkyl group, —OR^(22b) (wherein R^(22b) is a C1-C6 haloalkyl group),—S(O)_(m)R^(23b) (wherein R^(23b) is a C1-C6 haloalkyl group, and m is0, 1 or 2) or a halogen atom;

A compound represented by the formula (1-2) wherein R^(5b) is a C1-C6haloalkyl group, —OR^(22b) (wherein R^(22b) is a C1-haloalkyl group) or—S(O)_(m)R^(23b) (wherein R^(23b) a C1-haloalkyl group, and m is 0, 1 or2);

A compound represented by the formula (1-2) wherein R^(5b) is a C1-C6perfluoroalkyl group, —OR^(22b) (wherein R^(2b) is a C1-C6perfluoroalkyl group) or —S(O)_(m)R^(23b) (wherein R^(23b) is a C1-C6perfluoroalkyl group);

A compound represented by the formula (1-2) wherein R^(5b) is atrifluoromethyl group, —CF₂CF₃, —CF₂CF₂CF₃, —CF(CF₃)₂, —OCF₃, —OCF₂CF₃,—SCF₃, —S(O)CF₃, —S(O)₂CF₃, —SCF₂CF₃, —S(O)CF₂CF₃, —S(O)₂CF₂CF₃, SF₅, afluorine atom, a chlorine atom, a bromine atom or an iodine atom;

A compound represented by the formula (1-2) wherein when A^(3b) is═CR^(9b)—, R^(9b) is a fluorine atom, a chlorine atom, a bromine atom,an iodine atom or a hydrogen atom;

A compound represented by the formula (1-2) wherein when A^(3b) is═CR^(9b)—, R^(9b) is a fluorine atom or a hydrogen atom;

A compound represented by the formula (1-3) wherein A^(3b) is a nitrogenatom;

A compound represented by the formula (1-3) wherein A^(3b) is ═CR^(9b)—compound;

A compound represented by the formula (1-3) wherein R^(1b) is an ethylgroup;

A compound represented by the formula (1-3) wherein R^(3b) is a methylgroup, a fluoromethyl group, a difluoromethyl group, a trifluoromethylgroup, an ethyl group, an ethenyl group, an ethynyl group, afluoromethyl group, a difluoromethyl group, a trifluoromethyl group,—CF₂CF₃, —CF₂CF₂CF₃, —CF(CF₃)₂, —CF₂CF₂CF₂CF₃, —OCF₃, —OCF₂CF₃, —SCF₃,—S(O)CF₃, —S(O)₂CF₃, —SCF₂CF₃, —S(O)CF₂CF₃, —S(O)₂CF₂CF₃, a fluorineatom, a chlorine atom, a bromine atom, an iodine atom or a hydrogenatom;

A compound represented by the formula (1-3) wherein R^(5b) is a C1-C6haloalkyl group, —OR^(22b) (wherein R^(22b) is a C1-C6 haloalkyl group),—S(O)_(m)R^(23b) (wherein R^(23b) is a C1-C6 haloalkyl group, and m is0, 1 or 2), —SF₅ or a halogen atom;

A compound represented by the formula (1-3) wherein R^(5b) is a C1-C6haloalkyl group, —OR^(22b) (wherein R^(22b) is a C1-C6 haloalkyl group),—S(O)_(m)R^(23b) (wherein R^(23b) is a C1-C6 haloalkyl group, and m is0, 1 or 2) or —SF₅;

A compound represented by the formula (1-3) wherein R^(5b) is a C1-C6haloalkyl group, —OR^(22b) (wherein R^(22b) is a C1-C6 haloalkyl group),—S(O)_(m)R^(23b) (wherein R^(23b) is a C1-C6 haloalkyl group, and m is0, 1 or 2) or a halogen atom;

A compound represented by the formula (1-3) wherein R^(5b) is a C1-C6haloalkyl group, —OR^(22b) (wherein R^(22b) is a C1-C6 haloalkyl group)or —S(O)_(m)R^(23b) (wherein R^(23b) is a C1-C6 haloalkyl group, and mis 0, 1 or 2);

A compound represented by the formula (1-3) wherein R^(5b) is a C1-C6perfluoroalkyl group, —OR^(22b) (wherein R^(22b) is a C1-C6perfluoroalkyl group) or —S(O)_(m)R^(23b) (wherein R^(23b) is a C1-C6perfluoroalkyl group);

A compound represented by the formula (1-3) wherein R^(5b) is atrifluoromethyl group, —CF₂CF₃, —CF₂CF₂CF₃, —CF(CF₃)₂, —OCF₃, —OCF₂CF₃,—SCF₃, —S(O)CF₃, —S(O)₂CF₃, —SCF₂CF₃, —S(O)CF₂CF₃, —S(O)₂CF₂CF₃, SF₅, afluorine atom, a chlorine atom, a bromine atom or an iodine atom;

A compound represented by the formula (1-3) wherein when A^(3b) is═CR^(9b)—, R^(9b) is a fluorine atom, a chlorine atom, a bromine atom,an iodine atom or a hydrogen atom;

A compound represented by the formula (1-3) wherein when A^(3b) is═CR^(9b)—, R⁹ is a fluorine atom or a hydrogen atom;

A compound represented by the formula (1-4) wherein A^(3b) is a nitrogenatom;

A compound represented by the formula (1-4) wherein A^(3b) is ═CR^(9b)—compound;

A compound represented by the formula (1-4) wherein R^(1b) is an ethylgroup;

A compound represented by the formula (1-4) wherein R^(3b) is a methylgroup, a fluoromethyl group, a difluoromethyl group, a trifluoromethylgroup, an ethyl group, an ethenyl group, an ethynyl group, afluoromethyl group, a difluoromethyl group, a trifluoromethyl group,—CF₂CF₃, —CF₂CF₂CF₃, —CF(CF₃)₂, —CF₂CF₂CF₂CF₃, —OCF₃, —OCF₂CF₃, —SCF₃,—S(O)CF₃, —S(O)₂CF₃, —SCF₂CF₃, —S(O)CF₂CF₃, —S(O)₂CF₂CF₃, a fluorineatom, a chlorine atom, a bromine atom, an iodine atom or a hydrogenatom;

A compound represented by the formula (1-4) wherein R^(5b) is a C1-C6haloalkyl group, —OR^(22b) (wherein R^(22b) is a C1-C6 haloalkyl group),—S(O)_(m)R^(23b) (wherein R^(23b) is a C1-C6 haloalkyl group, and m is0, 1 or 2), —SF₅ or a halogen atom;

A compound represented by the formula (1-4) wherein R^(5b) is a C1-C6haloalkyl group, —OR^(22b) (wherein R^(22b) is a C1-C6 haloalkyl group),—S(O)_(m)R^(23b) (wherein R^(23b) is a C1-C6 haloalkyl group, and m is0, 1 or 2) or —SF₅;

A compound represented by the formula (1-4) wherein R^(5b) is a C1-C6haloalkyl group, —OR^(22b) (wherein R^(22b) is a C1-C6 haloalkyl group),—S(O)_(m)R^(23b) (wherein R^(23b) is a C1-C6 haloalkyl group, and m is0, 1 or 2) or a halogen atom;

A compound represented by the formula (1-4) wherein R^(5b) is a C1-C6haloalkyl group, —OR^(22b) (wherein R^(22b) is a C1-C6 haloalkyl group)or —S(O)_(m)R^(23b) (wherein R^(23b) is a C1-C6 haloalkyl group, and mis 0, 1 or 2);

A compound represented by the formula (1-4) wherein R^(5b) is a C1-C6perfluoroalkyl group, —OR^(22b) (wherein R^(22b) is a C1-C6perfluoroalkyl group) or —S(O)_(m)R^(23b) (wherein R^(23b) is a C1-C6perfluoroalkyl group);

A compound represented by the formula (1-4) wherein R^(5b) is atrifluoromethyl group, —CF₂CF₃, —CF₂CF₂CF₃, —CF(CF₃)₂, —OCF₃, —OCF₂CF₃,—SCF₃, —S(O)CF₃, —S(O)₂CF₃, —SCF₂CF₃, —S(O)CF₂CF₃, —S(O)₂CF₂CF₃, SF₅, afluorine atom, a chlorine atom, a bromine atom or an iodine atom;

A compound represented by the formula (1-4) wherein when A^(3b) is═CR^(9b)—, R^(9b) is a fluorine atom, a chlorine atom, a bromine atom,an iodine atom or a hydrogen atom;

A compound represented by the formula (1-4) wherein when A^(3b) is═CR^(9b)—, R^(9b) is a fluorine atom or a hydrogen atom;

A compound represented by the formula (1-5) wherein A^(3a) is a nitrogenatom;

A compound represented by the formula (1-5) wherein A^(3a) is ═CR^(9a)—compound;

A compound represented by the formula (1-5) wherein R^(1a) is a C1-C6alkyl group optionally substituted by one or more atoms or groupsselected from the group consisting of a halogen atom and a cyclopropylgroup (wherein the cyclopropyl group is optionally substituted by one ormore halogen atoms or one or more C1-C3 alkyl groups);

A compound represented by the formula (1-5) wherein R^(1a) is a C1-C6alkyl group, a C1-C6 haloalkyl group, or a C4-C9 cyclopropylalkyl group(wherein the cyclopropyl group is optionally substituted by one or morehalogen atoms or one or more C1-C3 alkyl groups);

A compound represented by the formula (1-5) wherein R^(1a) is a C2-C6alkyl group, a C1-C6 haloalkyl group or C4-C9 cyclopropylalkyl group(wherein the cyclopropyl group is optionally substituted by one or morehalogen atoms or one or more C1-C3 alkyl groups);

A compound represented by the formula (1-5) wherein R^(1a) is a methylgroup, an ethyl group, a propyl group, an isopropyl group, atrifluoromethyl group, a 2,2,2-trifluoroethyl group or acyclopropylmethyl group;

A compound represented by the formula (1-5) wherein R^(1a) is an ethylgroup or a cyclopropylmethyl group;

A compound represented by the formula (1-5) wherein R^(1a) is an ethylgroup;

A compound represented by the formula (1-5) wherein R^(3a) is a C1-C6alkyl group optionally substituted by one or more halogen atoms, a C2-C6alkenyl group optionally substituted by one or more halogen atoms, aC2-C6 alkynyl group optionally substituted by one or more halogen atoms,pyridyl group (wherein the pyridyl group is optionally substituted byone or more atoms or substituents selected from the group consisting ofa halogen atom, a C1-C3 alkyl group optionally substituted by one ormore halogen atoms, and a C1-C3 alkoxy group optionally substituted byone or more halogen atoms), a pyrimidinyl group (wherein the pyrimidinylgroup is optionally substituted by one or more atoms or substituentsselected from the group consisting of a halogen atom, a C1-C3 alkylgroup optionally substituted by one or more halogen atoms, and a C1-C3alkoxy group optionally substituted by one or more halogen atoms),—OR^(20a) (wherein R^(20a) is a C1-C6 alkyl group optionally substitutedby one or more halogen atoms), —S(O)_(m)R^(21a) (wherein R^(21a) is aC1-C6 alkyl group optionally substituted by one or more halogen atoms,and m is 0, 1 or 2), a halogen atom or a hydrogen atom;

A compound represented by the formula (1-5) wherein R^(3a) is a C1-C6alkyl group optionally substituted by one or more halogen atoms,—OR^(20a) (wherein R^(20a) represents a C1-C6 alkyl group optionallysubstituted by one or more halogen atoms), —S(O)_(m)R^(21a) (whereinR^(21a) represents a C1-C6 alkyl group optionally substituted by one ormore halogen atoms, m represents 0, 1 or 2), a halogen atom or ahydrogen atom;

A compound represented by the formula (1-5) wherein R^(3a) is a methylgroup, a fluoromethyl group, a difluoromethyl group, a trifluoromethylgroup, an ethyl group, an ethenyl group, an ethynyl group, afluoromethyl group, a difluoromethyl group, a trifluoromethyl group,—CF₂CF₃, —CF₂CF₂CF₃, —CF(CF₃)₂, —CF₂CF₂CF₂CF₃, —OCF₃, —OCF₂CF₃, —SCF₃,—S(O)CF₃, —S(O)₂CF₃, —SCF₂CF₃, —S(O)CF₂CF₃, —S(O)₂CF₂CF₃, a 2-pyridylgroup, a 5-trifluoromethyl-2-pyridyl group, a 2-pyrimidinyl group, afluorine atom, a chlorine atom, a bromine atom, an iodine atom or ahydrogen atom;

A compound represented by the formula (1-5) wherein R^(3a) is a methylgroup, a fluoromethyl group, a difluoromethyl group, a trifluoromethylgroup, an ethyl group, an ethenyl group, an ethynyl group, afluoromethyl group, a difluoromethyl group, a trifluoromethyl group,—CF₂CF₃, —CF₂CF₂CF₃, —CF(CF₃)₂, —CF₂CF₂CF₂CF₃, —OCF₃, —OCF₂CF₃, —SCF₃,—S(O)CF₃, —S(O)₂CF₃, —SCF₂CF₃, —S(O)CF₂CF₃, —S(O)₂CF₂CF₃, a fluorineatom, a chlorine atom, a bromine atom, an iodine atom or a hydrogenatom;

A compound represented by the formula (1-5) wherein R^(2a) and R^(4a)both are a hydrogen atom;

A compound represented by the formula (1-5) wherein R^(5a) is a C1-C6haloalkyl group, —OR^(22a) (wherein R^(22a) is a C1-C6 haloalkyl group),—S(O)_(m)R^(23a) (wherein R^(23a) is a C1-C6 haloalkyl group, and m is0, 1 or 2), —SF₅ or a halogen atom;

A compound represented by the formula (1-5) wherein R^(5a) is a C1-C6haloalkyl group, —OR^(22a) (wherein R^(22a) is a C1-C6 haloalkyl group),—S(O)_(m)R^(23a) (wherein R^(23a) is a C1-C6 haloalkyl group, and m is0, 1 or 2) or —SF₅;

A compound represented by the formula (1-5) wherein R^(5a) is a C1-C6haloalkyl group, —OR^(22a) (wherein R^(22a) is a C1-C6 haloalkyl group),—S(O)_(m)R^(23a) (wherein R^(23a) is a C1-C6 haloalkyl group, and m is0, 1 or 2) or a halogen atom;

A compound represented by the formula (1-5) wherein R^(5a) is a C1-C6haloalkyl group, —OR^(22a) (wherein R^(22a) is a C1-C6 haloalkyl group)or —S(O)_(m)R^(23a) (wherein R^(23a) is a C1-C6 haloalkyl group, and mis 0, 1 or 2);

A compound represented by the formula (1-5) wherein R^(5a) is a C1-C6perfluoroalkyl group, —OR^(22a) (wherein R^(22a) is a C1-C6perfluoroalkyl group) or —S(O)_(m)R^(23a) (wherein R^(23a) is a C1-C6perfluoroalkyl group);

A compound represented by the formula (1-5) wherein R^(5a) is atrifluoromethyl group, —CF₂CF₃, —CF₂CF₂CF₃, —CF(CF₃)₂, —OCF₃, —OCF₂CF₃,—SCF₃, —S(O)CF₃, —S(O)₂CF₃, —SCF₂CF₃, S(O)CF₂CF₃, —S(O)₂CF₂CF₃, SF₅, afluorine atom, a chlorine atom, a bromine atom or an iodine atom;

A compound represented by the formula (1-5) wherein R^(70a) is ahydrogen atom, a methoxymethyl group, an ethoxymethyl group, a1-(methoxy)ethyl group or a 1-(ethoxy)ethyl group;

A compound represented by the formula (1-5) wherein when A^(3a) is═CR^(9a)—, R^(9a) is a halogen atom or a hydrogen atom;

A compound represented by the formula (1-5) wherein when A^(3a) is═CR^(9a)—, R^(9a) is a fluorine atom, a chlorine atom, a bromine atom,an iodine atom or a hydrogen atom;

A compound represented by the formula (1-5) wherein when A^(3a) is═CR^(9a)—, R^(9a) is a fluorine atom or a hydrogen atom;

A compound represented by the formula (1-6) wherein A^(3b) is a nitrogenatom;

A compound represented by the formula (1-6) wherein A^(3b) is ═CR^(9b)—compound;

A compound represented by the formula (1-6) wherein R^(1b) is an ethylgroup;

A compound represented by the formula (1-6) wherein R^(3b) is a methylgroup, a fluoromethyl group, a difluoromethyl group, a trifluoromethylgroup, an ethyl group, an ethenyl group, an ethynyl group, afluoromethyl group, a difluoromethyl group, a trifluoromethyl group,—CF₂CF₃, —CF₂CF₂CF₃, —CF(CF₃)₂, —CF₂CF₂CF₂CF₃, —OCF₃, —OCF₂CF₃, —SCF₃,—S(O)CF₃, —S(O)₂CF₃, —SCF₂CF₃; —S(O)CF₂CF₃, —S(O)₂CF₂CF₃, a fluorineatom, a chlorine atom, a bromine atom, an iodine atom or a hydrogenatom;

A compound represented by the formula (1-6) wherein R^(5b) is a C1-C6haloalkyl group, —OR^(22b) (wherein R^(22b) is a C1-C6 haloalkyl group),—S(O)_(m)R^(23b) (wherein R^(23b) is a C1-C6 haloalkyl group, and m is0, 1 or 2), —SF₅ or a halogen atom;

A compound represented by the formula (1-6) wherein R^(5b) is a C1-C6haloalkyl group, —OR^(22b) (wherein R^(22b) is a C1-C6 haloalkyl group),—S(O)_(m)R^(23b) (wherein R^(23b) is a C1-C6 haloalkyl group, and m is0, 1 or 2) or —SF₅;

A compound represented by the formula (1-6) wherein R^(5b) is a C1-C6haloalkyl group, —OR^(22b) (wherein R^(22b) is a C1-C6 haloalkyl group),—S(O)_(m)R^(23b) (wherein R^(23b) is a C1-C6 haloalkyl group, and m is0, 1 or 2) or a halogen atom;

A compound represented by the formula (1-6) wherein R^(5b) is a C1-C6haloalkyl group, —OR^(22b) (wherein R^(22b) is a C1-C6 haloalkyl group)or —S(O)_(m)R^(23b) (wherein R^(23b) is a, C1-C6 haloalkyl group, and mis 0, 1 or 2);

A compound represented by the formula (1-6) wherein R^(5b) is a C1-C6perfluoroalkyl group, —OR^(22b) (wherein R^(22b) is a C1-C6perfluoroalkyl group) or —S(O)_(m)R^(23b) (wherein R^(23b) is a C1-C6perfluoroalkyl group);

A compound represented by the formula (1-6) wherein R^(5b) is atrifluoromethyl group, —CF₂CF₃, —CF₂CF₂CF₃, —CF(CF₃)₂, —OCF₃, —OCF₂CF₃,—SCF₃, —S(O)CF₃, —S(O)₂CF₃, —SCF₂CF₃, —S(O)CF₂CF₃, —S(O)₂CF₂CF₃, SF₅, afluorine atom, a chlorine atom, a bromine atom or an iodine atom;

A compound represented by the formula (1-6) wherein R^(70b) is ahydrogen atom, a methoxymethyl group, an ethoxymethyl group, a1-(methoxy)ethyl group or a 1-(ethoxy)ethyl group;

A compound represented by the formula (1-6) wherein when A^(3b) is═CR^(9b)—, R^(9b) is a fluorine atom, a chlorine atom, a bromine atom,an iodine atom or a hydrogen atom;

A compound represented by the formula (1-6) wherein when A^(3b) is═CR^(9b)—, R^(9b) is a fluorine atom or a hydrogen atom;

A fused heterocyclic compound represented by the formula (1-7):

whereinA^(1c) represents —NR^(7c)—, an oxygen atom or a sulfur atom;A^(2c) represents a nitrogen atom or ═CR^(8c)—,A^(3c) represents a nitrogen atom or ═CR^(9c)—,R^(1c) represents a C1-C6 chain hydrocarbon group optionally substitutedby one or more atoms or groups selected from Group X^(c) or a C3-C6alicyclic hydrocarbon group optionally substituted by one or more atomsor groups selected from Group Y^(c),R^(2c) and R^(4c) are the same or different and each represents a C1-C6chain hydrocarbon group optionally substituted by one or more halogenatoms, —OR^(10c), —S(O)_(m)R^(10c), —NR^(10c)R^(11c), —CO₂R^(10c),—C(O)R¹⁰, a cyano group, a nitro group, a halogen atom or a hydrogenatom,R^(3c) represents a C1-C6 chain hydrocarbon group optionally substitutedby one or more halogen atoms, a phenyl group optionally substituted byone or more atoms or groups selected from Group Z^(c), a 5-memberedheterocyclic group optionally substituted by one or more atoms or groupsselected from Group Z^(c), a 6-membered heterocyclic group optionallysubstituted by one or more atoms or groups selected from Group Z^(c),—OR^(10c), —S(O)_(m)R^(10c), —NR^(10c)R^(11c), —CO₂R^(10c),—C(O)R^(10c), a cyano group, a nitro group, a halogen atom or a hydrogenatom,R^(5c) and R^(6c) are the same or different and each represents a C1-C6chain hydrocarbon group optionally substituted by one or more atoms orgroups selected from Group X^(c), a phenyl group optionally substitutedby one or more atoms or groups selected from Group Z^(c), a 5-memberedheterocyclic group optionally substituted by one or more atoms or groupsselected from Group Z^(c), a 6-membered heterocyclic group optionallysubstituted by one or more atoms or groups selected from Group Z^(c),—OR^(10c), —S(O)_(m)R^(10c), —S(O)₂NR^(10c)R^(11c), —NR^(10c)R^(11c),—CO₂R^(10c), —C(O)R^(10c), —SF₅, a cyano group, a nitro group, a halogenatom or a hydrogen atom,R^(7c) represents a C1-C6 chain hydrocarbon group optionally substitutedby one or more atoms or groups selected from Group W^(c), —CO₂R^(10c),—C(O)R^(10c), or a C3-C6 alicyclic hydrocarbon group optionallysubstituted by one or more atoms or groups selected from Group Y^(c),R^(8c) and R^(9c) are the same or different and each represents a C1-C6chain hydrocarbon group optionally substituted by one or more halogenatoms, —OR^(10c), —S(O)_(m)R^(10c), —NR¹⁰CR^(11c), —CO₂R^(10c),—C(O)R^(10c), a cyano group, a nitro group, a halogen atom or a hydrogenatom,R^(10c) and R^(11c) are the same or different and each represents aC1-C6 chain hydrocarbon group optionally substituted by one or morehalogen atoms or a hydrogen atom,m represents 0, 1 or 2, andn represents 0, 1 or 2.wherein R^(5c) and R^(6c) do not represents a hydrogen atom at the sametime, and in the —S(O)_(m)R^(10c), R^(10c) does not a hydrogen atom whenm is 1 or 2,Group X^(c): the group consisting of a C1-C6 alkoxy group optionallysubstituted by one or more halogen atoms, a C2-C6 alkenyloxy groupoptionally substituted by one or more halogen atoms, a C2-C6 alkynyloxygroup optionally substituted by one or more halogen atoms, a C1-C6alkylsulfanyl group optionally substituted by one or more halogen atoms,a C1-C6 alkylsulfinyl group optionally substituted by one or morehalogen atoms, a C1-C6 alkylsulfonyl group optionally substituted by oneor more halogen atoms, a hydroxy group and a halogen atom,Group Y^(c): the group consisting of a C1-C6 chain hydrocarbon groupoptionally substituted by one or more halogen atoms, a C1-C6 alkoxygroup optionally substituted by one or more halogen atoms and a halogenatom,Group Z^(c): the group consisting of a C1-C6 chain hydrocarbon groupoptionally substituted by one or more halogen atoms, a C1-C6 alkoxygroup optionally substituted by one or more halogen atoms, a C1-C6alkylsulfanyl group optionally substituted by one or more halogen atoms,a C1-C6 alkylsulfinyl group optionally substituted by one or morehalogen atoms, a C1-C6 alkylsulfonyl group optionally substituted by oneor more halogen atoms, a C2-C6 alkylcarbonyl group optionallysubstituted by one or more halogen atoms, a C2-C6 alkoxycarbonyl groupoptionally substituted by one or more halogen atoms, a C1-C6 alkylaminogroup optionally substituted by one or more halogen atoms, a C2-C8dialkylamino group optionally substituted by one or more halogen atoms,a halogen atom, a cyano group and a nitro group,Group W^(c): the group consisting of a C1-C6 alkoxy group optionallysubstituted by one or more halogen atoms, a C2-C6 alkenyloxy groupoptionally substituted by one or more halogen atoms, a C2-C6 alkynyloxygroup optionally substituted by one or more halogen atoms, a C1-C6alkylsulfanyl group optionally substituted by one or more halogen atoms,a C2-C6 alkylcarbonyl group optionally substituted by one or morehalogen atoms, a C2-C6 alkoxycarbonyl group optionally substituted byone or more halogen atoms, a C3-C6 cycloalkyl group optionallysubstituted by one or more halogen atoms, a C1-C6 alkylsulfinyl groupoptionally substituted by one or more halogen atoms, a C1-C6alkylsulfonyl group optionally substituted by one or more halogen atoms,hydroxy group, a halogen atom and a cyano group.

A compound represented by the formula (1-7) wherein A^(1c) is —NR^(7c)—;

A compound represented by the formula (1-7) wherein A^(1c) is an oxygenatom;

A compound represented by the formula (1-7) wherein A^(1c) is a sulfuratom;

A compound represented by the formula (1-7) wherein A^(1c) is —NR^(7c)—,R^(7c) is a C1-C6 chain hydrocarbon group optionally substituted by oneor more halogen atoms, a C1-C6 chain hydrocarbon group substituted byone C1-C6 alkoxy group optionally substituted by one or more halogenatoms, or a cyclopropyl group;

A compound represented by the formula (1-7) wherein A^(1c) is —NR^(7c)—,R^(7c) is a methyl group, an ethyl group, a methoxymethyl group or anethoxymethyl group;

A compound represented by the formula (1-7) wherein A^(2c) is a nitrogenatom;

A compound represented by the formula (1-7) wherein A^(2c) is ═CR^(8c)—;

A compound represented by the formula (1-7) wherein A^(2c) is ═CH—;

A compound represented by the formula (1-7) wherein A^(3c) is a nitrogenatom;

A compound represented by the formula (1-7) wherein A^(3c) is ═CR^(9c)—;

A compound represented by the formula (1-7) wherein A^(3c) is a nitrogenatom or ═CR^(9c)—, and R^(9c) is a halogen atom or a hydrogen atom;

A compound represented by the formula (1-7) wherein A^(2c) is ═CR^(8c)—,A^(3c) is ═CR^(9c)—;

A compound represented by the formula (1-7) wherein A^(2c) is a nitrogenatom, A^(3c) is ═CR^(9c)—;

A compound represented by the formula (1-7) wherein A^(2c) is ═CR^(8c)—,A^(3c) is a nitrogen atom;

A compound represented by the formula (1-7) wherein A^(2c) is a nitrogenatom, A^(3c) is a nitrogen atom;

A compound represented by the formula (1-7) wherein A^(2c) is ═CR^(8c)—,R^(8c) is a hydrogen atom, A^(3c) is a nitrogen atom;

A compound represented by the formula (1-7) wherein A^(1c) is —NR^(7c)—,A^(2c) is ═CR^(8c)—, A^(3c) is ═CR^(9c)—;

A compound represented by the formula (1-7) wherein A^(1c) is —NR^(7c)—,A^(2c) is a nitrogen atom, A^(3c) is ═CR^(9c)—;

A compound represented by the formula (1-7) wherein A^(1c) is —NR^(7c)—,A^(2c) is ═CR^(8c)—, A^(3c) is a nitrogen atom;

A compound represented by the formula (1-7) wherein A^(1c) is —NR^(7c)—,A^(2c) is ═CR^(8c)—, R^(8c) is a hydrogen atom, A^(3c) is a nitrogenatom;

A compound represented by the formula (1-7) wherein A^(1c) is —NR^(7c)—,R^(7c) is a methyl group, and A² is ═CR^(8c)—, R⁸ is a hydrogen atom,A^(3c) is a nitrogen atom;

A compound represented by the formula (1-7) wherein A^(1c) is —NR^(7c)—,A^(2c) is a nitrogen atom, A^(3c) is a nitrogen atom;

A compound represented by the formula (1-7) wherein A^(1c) is an oxygenatom, and A^(2c) is ═CR^(8c)—, A^(3c) is ═CR^(9c)—;

A compound represented by the formula (1-7) wherein A^(1c) is an oxygenatom, and A²C is a nitrogen atom, A^(3c) is ═CR^(9c)—;

A compound represented by the formula (1-7) wherein A^(1c) is an oxygenatom, and A^(2c) is ═CR^(8c)—, A^(3c) is a nitrogen atom;

A compound represented by the formula (1-7) wherein A^(1c) is an oxygenatom, and A^(2c) is ═CR^(8c)—, R^(8c) is a hydrogen atom, A^(3c) is anitrogen atom;

A compound represented by the formula (1-7) wherein A^(1c) is an oxygenatom, and A^(2c) is a nitrogen atom, A^(3c) is a nitrogen atom;

A compound represented by the formula (1-7) wherein A^(1c) is a sulfuratom, and A^(2c) is ═CR^(8c)—, A^(3c) is ═CR^(9c)—;

A compound represented by the formula (1-7) wherein A^(1c) is a sulfuratom, and A^(2c) is a nitrogen atom, A^(3c) is ═CR^(9c)—;

A compound represented by the formula (1-7) wherein A^(1c) is a sulfuratom, and A^(2c) is ═CR^(8c)—, A^(3c) is a nitrogen atom;

A compound represented by the formula (1-7) wherein A^(1c) is a sulfuratom, and A^(2c) is ═CR^(8c)—, R^(8c) is a hydrogen atom, A^(3c) is anitrogen atom;

A compound represented by the formula (1-7) wherein A^(1c) is a sulfuratom, and A^(2c) is a nitrogen atom, A^(3c) is a nitrogen atom;

A compound represented by the formula (1-7) wherein R^(1c) is a C1-C6chain hydrocarbon group optionally substituted by one or more halogenatoms;

A compound represented by the formula (1-7) wherein R^(1c) is a C1-C6alkyl group optionally substituted by one or more halogen atoms;

A compound represented by the formula (1-7) wherein R^(2c) and R^(4c)are the same or different and each represents a hydrogen atom or ahalogen atom, R^(3c) is a C1-C6 chain hydrocarbon group optionallysubstituted by one or more halogen atoms, —OR^(10c), a halogen atom or ahydrogen atom;

A compound represented by the formula (1-7) wherein R^(2c) and R^(4c)both are a hydrogen atom,

R^(3c) is a C1-C6 chain hydrocarbon group optionally substituted by oneor more halogen atoms, a halogen atom or a hydrogen atom;

A compound represented by the formula (1-7) wherein R^(2c) and R^(4c)both are a hydrogen atom, R^(3c) is a phenyl group optionallysubstituted by one or more halogen atoms or a C1-C3 alkyl groupoptionally substituted by one or more halogen atoms, a 5-memberedheterocyclic group optionally substituted by one or more halogen atomsor a C1-C3 alkyl group optionally substituted by one or more halogenatoms or a 6-membered heterocyclic group optionally substituted by oneor more halogen atoms or a C1-C3 alkyl group optionally substituted byone or more halogen atoms;

A compound represented by the formula (1-7) wherein R^(2c), R^(3c) andR^(4c) is a hydrogen atom;

A compound represented by the formula (1-7) wherein R^(5c) and R^(6c)are the same or different and each represents a C1-C6 chain hydrocarbongroup optionally substituted by one or more halogen atoms, —OR^(10c),—S(O)_(m)R^(10c), a halogen atom or a hydrogen atom;

A compound represented by the formula (1-7) wherein R^(5c) is a C1-C6chain hydrocarbon group optionally substituted by one or more halogenatoms, —OR^(10c), —S(O)_(m)R^(10c) or a halogen atom, R^(6c) is ahydrogen atom;

A compound represented by the formula (1-7) wherein R^(5c) is a C1-C3alkyl group substituted by one or more fluorine atoms, a C1-C3 alkoxygroup substituted by one or more fluorine atoms, a C1-C3 alkylsulfanylgroup substituted by one or more fluorine atoms, a C1-C3 alkylsulfinylgroup substituted by one or more fluorine atoms, a C1-C3 alkylsulfonylgroup substituted by one or more fluorine atoms or a halogen atom,R^(6c) is a hydrogen atom;

A compound represented by the formula (1-7) wherein R^(1c) is a C1-C6chain hydrocarbon group optionally substituted by one or more halogenatoms, R^(2c) and R^(4c) are the same or different and each represents ahydrogen atom or a halogen atom, R^(3c) is a C1-C6 chain hydrocarbongroup optionally substituted by one or more halogen atoms, —OR^(10c), ahalogen atom or a hydrogen atom, R^(5c) and R^(6c) are the same ordifferent and each represents a C1-C6 chain hydrocarbon group optionallysubstituted by one or more halogen atoms, —OR^(10c), —S(O)_(m)R^(10c), ahalogen atom or a hydrogen atom, A^(1c) is —NR^(7c)—, R^(7c) is a C1-C6chain hydrocarbon group optionally substituted by one or more halogenatoms, a C1-C6 chain hydrocarbon group substituted by one C1-C6 alkoxygroup optionally substituted by one or more halogen atoms, or acyclopropyl group, and A²C is ═CH—, and A^(3c) is a nitrogen atom or═CR^(9c)—, and R^(9c) is a halogen atom or a hydrogen atom;

A compound represented by the formula (1-7) wherein A^(1c) is —NR^(7c)—,an oxygen atom or a sulfur atom, R^(7c) is a C1-C6 chain hydrocarbongroup optionally substituted by one or more halogen atoms, a C1-C6 chainhydrocarbon group substituted by one C1-C6 alkoxy group optionallysubstituted by one or more halogen atoms or a C1-C6 chain hydrocarbongroup, A^(2c) is ═CR^(8c)—, A^(3c) is a nitrogen atom or ═CR^(9c)—, andR^(9c) is a halogen atom or a hydrogen atom, R^(1c) is a C1-C6 chainhydrocarbon group optionally substituted by one or more halogen atoms,R^(2c) and R^(4c) are the same or different and each represents ahalogen atom or a hydrogen atom, R^(3c) is a C1-C6 chain hydrocarbongroup optionally substituted by one or more halogen atoms, —OR^(10c),—S(O)_(m)R^(10c) a halogen atom or a hydrogen atom, R^(5c) is a C1-C6chain hydrocarbon group optionally substituted by one or more halogenatoms, —OR^(10c), —S(O)_(m)R^(10c) or a halogen atom, R^(6c) is ahydrogen atom, R^(10c) is a C1-C6 alkyl group optionally substituted byone or more halogen atoms;

A compound represented by the formula (1-7) wherein A^(1c) is —NR^(7c)—,R^(7c) is a C1-C6 alkyl group, A^(2c) is ═CR^(8c)—, A^(3c) is ═CR^(9c)—,and R^(1c) is a C1-C3 alkyl group optionally substituted by one or morefluorine atoms, R^(2c) and R^(4c) both are a hydrogen atom, R^(3c) is aC1-C3 alkyl group optionally substituted by one or more fluorine atoms,a halogen atom or a hydrogen atom, R^(5c) is a C1-C3 alkyl groupsubstituted by one or more fluorine atoms, a C1-C3 alkoxy groupsubstituted by one or more fluorine atoms, a C1-C3 alkylsulfanyl groupsubstituted by one or more fluorine atoms, a C1-C3 alkylsulfinyl groupsubstituted by one or more fluorine atoms, a C1-C3 alkylsulfonyl groupsubstituted by one or more fluorine atoms or a halogen atom, R^(6c) is ahydrogen atom;

A compound represented by the formula (1-7) wherein A^(1c) is —NR^(7c)—,R^(7c) is a C1-C6 alkyl group, A^(2c) is ═CR^(8c)—, R^(8c) is a hydrogenatom, A^(3c) is a nitrogen atom, R^(1c) is a C1-C3 alkyl groupoptionally substituted by one or more fluorine atoms, R^(2c) and R^(4c)both are a hydrogen atom, R^(3c) is a C1-C3 alkyl group optionallysubstituted by one or more fluorine atoms, a halogen atom or a hydrogenatom, R^(5c) is a C1-C3 alkyl group substituted by one or more fluorineatoms, a C1-C3 alkoxy group substituted by one or more fluorine atoms, aC1-C3 alkylsulfanyl group substituted by one or more fluorine atoms, aC1-C3 alkylsulfinyl group substituted by one or more fluorine atoms, aC1-C3 alkylsulfonyl group substituted by one or more fluorine atoms or ahalogen atom, R^(6c) is a hydrogen atom;

A compound represented by the formula (1-7) wherein A^(1c) is a sulfuratom, and A^(2c) is ═CR^(8c)—, A^(3c) is ═CR^(9c)—, and R^(1c) is aC1-C3 alkyl group optionally substituted by one or more fluorine atoms,R^(2c) and R^(4c) both are a hydrogen atom, R^(3c) is a C1-C3 alkylgroup optionally substituted by one or more fluorine atoms, a halogenatom or a hydrogen atom, R^(5c) is a C1-C3 alkyl group substituted byone or more fluorine atoms, a C1-C3 alkoxy group substituted by one ormore fluorine atoms, a C1-C3 alkylsulfanyl group substituted by one ormore fluorine atoms, a C1-C3 alkylsulfinyl group substituted by one ormore fluorine atoms, a C1-C3 alkylsulfonyl group substituted by one ormore fluorine atoms or a halogen atom, R^(6c) is a hydrogen atom;

A compound represented by the formula (1-7) wherein A^(1c) is a sulfuratom, and A^(2c) is ═CR^(8c)—, R^(8c) is a hydrogen atom, A^(3c) is anitrogen atom, R^(1c) is a C1-C3 alkyl group optionally substituted byone or more fluorine atoms, R^(2c) and R^(4c) both are a hydrogen atom,R^(3c) is a C1-C3 alkyl group optionally substituted by one or morefluorine atoms, a halogen atom or a hydrogen atom, R^(5c) is a C1-C3alkyl group substituted by one or more fluorine atoms, a C1-C3 alkoxygroup substituted by one or more fluorine atoms, a C1-C3 alkylsulfanylgroup substituted by one or more fluorine atoms, a C1-C3 alkylsulfinylgroup substituted by one or more fluorine atoms, a C1-C3 alkylsulfonylgroup substituted by one or more fluorine atoms or a halogen atom,R^(6c) is a hydrogen atom;

A compound represented by the formula (1-7) wherein A^(1c) is —NR^(7c)—,R^(7c) is a methyl group, an ethyl group, a methoxymethyl group or anethoxymethyl group, R^(1c) is a methyl group, an ethyl group, a propylgroup, an isopropyl group, butyl group, sec-butyl group, an isobutylgroup, tert-butyl group, cyclopropyl group, a trifluoromethyl group,2,2,2-trifluoroethyl group, R^(2c) and R^(4c) both are a hydrogen atom,R^(3c) is a methyl group, a trifluoromethyl group, a trifluoromethoxygroup, a chlorine atom, a bromine atom, an iodine atom or a hydrogenatom, R^(5c) is a trifluoromethyl group, a difluoromethyl group, afluoromethyl group, a pentafluoroethyl group, a heptafluoroisopropylgroup, a trifluoromethoxy group, a trifluoromethylsulfanyl group, atrifluoromethylsulfinyl group, trifluoromethylsulfonyl group, a bromineatom or an iodine atom, R^(6c) is a hydrogen atom;

A fused heterocyclic compound represented by the formula (1-8):

whereinA^(1d) represents —NR^(7d)— or a sulfur atom,A^(3d) represents a nitrogen atom or ═CR^(9d)—,R^(1d) represents a C1-C6 chain hydrocarbon group optionally substitutedby one or more halogen atoms,R^(2d) and R^(4d) are the same or different and each represents a C1-C6chain hydrocarbon group optionally substituted by one or more halogenatoms, a halogen atom or a hydrogen atom,R^(3d) represents a C1-C6 chain hydrocarbon group optionally substitutedby one or more halogen atoms, —OR^(10d), a halogen atom or a hydrogenatom,R^(5d) represents a C1-C6 chain hydrocarbon group optionally substitutedby one or more halogen atoms, —OR^(10d), —S(O)_(m)R^(10d), a bromineatom or an iodine atom,R^(7d) represents a C1-C6 chain hydrocarbon group optionally substitutedby one or more halogen atoms,R^(9d) represents a halogen atom or a hydrogen atom,R^(10d) represents a C1-C6 chain hydrocarbon group optionallysubstituted by one or more halogen atoms,m represents 0, 1 or 2, andn represents 0, 1 or 2;

A compound represented by the formula (1-8) wherein A^(1d) is —NR^(7d)—;

A compound represented by the formula (1-8) wherein A^(1d) is a sulfuratom;

A compound represented by the formula (1-8) wherein A^(3d) is a nitrogenatom;

A compound represented by the formula (1-8) wherein A^(3d) is ═CR^(9d)—;

A compound represented by the formula (1-8) wherein A^(1d) is —NR^(7d)—or a sulfur atom, R^(7d) is a methyl group, and A^(3d) is a nitrogenatom;

A compound represented by the formula (1-8) wherein A^(1d) is —NR^(7d)—,and A^(3d) is ═CR^(9d)—;

A compound represented by the formula (1-8) wherein A^(1d) is a sulfuratom, and A^(3d) is ═CR^(9d)—;

A compound represented by the formula (1-8) wherein A^(1d) is —NR^(7d)—,and A^(3d) is a nitrogen atom;

A compound represented by the formula (1-8) wherein A^(1d) is a sulfuratom, and A^(3d) is a nitrogen atom;

A compound represented by the formula (1-8) wherein R^(1d) is a C1-C3alkyl group;

A compound represented by the formula (1-8) wherein R^(2d) and R^(4d) isa hydrogen atom, R^(3d) is a chlorine atom, a bromine atom, atrifluoromethyl group or a hydrogen atom;

A compound represented by the formula (1-8) wherein R^(2d), R^(3d) andR^(4d) is a hydrogen atom;

A compound represented by the formula (1-8) wherein R^(5d) is a C1-C3chain hydrocarbon group substituted by one or more fluorine atoms, aC1-C3 alkoxy group substituted by one or more fluorine atoms, a C1-C3alkylsulfanyl group substituted by one or more fluorine atoms, a C1-C3alkylsulfinyl group substituted by one or more fluorine atoms or a C1-C3alkylsulfonyl group substituted by one or more fluorine atoms;

A compound represented by the formula (1-8) wherein R^(5d) is atrifluoromethyl group, a pentafluoroethyl group, a heptafluoroisopropylgroup, a trifluoromethoxy group, a trifluoromethylsulfanyl group, atrifluoromethylsulfinyl group or a trifluoromethylsulfonyl group;

A compound represented by the formula (1-8) wherein A^(1d) is —NR^(7d)—or a sulfur atom, R^(7d) is a methyl group, and A^(3d) is a nitrogenatom, R^(1d) is an ethyl group, R^(2d) and R^(4d) are the same ordifferent and each represents a halogen atom or a hydrogen atom, R^(3d)is a trifluoromethyl group, a halogen atom or a hydrogen atom, R^(5d) isa C1-C3 chain hydrocarbon group substituted by one or more fluorineatoms, a C1-C3 alkoxy group substituted by one or more fluorine atoms, aC1-C3 alkylsulfanyl group substituted by one or more fluorine atoms, aC1-C3 alkylsulfinyl group substituted by one or more fluorine atoms or aC1-C3 alkylsulfonyl group substituted by one or more fluorine atoms;

A compound represented by the formula (1-8) wherein A^(1d) is —NR^(7d)—,and R^(7d) is a methyl group, and A^(3d) is ═CR^(9d)—, and R^(1d) is anethyl group, R^(2d) and R^(4d) are the same or different and eachrepresents a halogen atom or a hydrogen atom, R^(3d) is atrifluoromethyl group, a halogen atom or a hydrogen atom, R^(5d) is aC1-C3 chain hydrocarbon group substituted by one or more fluorine atoms,a C1-C3 alkoxy group substituted by one or more fluorine atoms, a C1-C3alkylsulfanyl group substituted by one or more fluorine atoms, a C1-C3alkylsulfinyl group substituted by one or more fluorine atoms or a C1-C3alkylsulfonyl group substituted by one or more fluorine atoms;

A compound represented by the formula (1-8) wherein A^(1d) is —NR^(7d)—,and R^(7d) is a methyl group or a hydrogen atom, A^(3d) is a nitrogenatom, R^(1d) is an ethyl group, R^(2d) and R^(4d) are the same ordifferent and each represents a halogen atom or a hydrogen atom, R^(3d)is a trifluoromethyl group, a halogen atom or a hydrogen atom, R^(5d) isa C1-C3 chain hydrocarbon group substituted by one or more fluorineatoms, a C1-C3 alkoxy group substituted by one or more fluorine atoms, aC1-C3 alkylsulfanyl group substituted by one or more fluorine atoms, aC1-C3 alkylsulfinyl group substituted by one or more fluorine atoms or aC1-C3 alkylsulfonyl group substituted by one or more fluorine atoms;

A compound represented by the formula (1-8) wherein A^(1d) is —NR^(7d)—or a sulfur atom, R^(7d) is a methyl group, and A^(3d) is ═CR^(9d)—, andR^(1d) is an ethyl group, R^(2d) and R^(4d) is a hydrogen atom, R^(3d)is a chlorine atom, a bromine atom, a trifluoromethyl group or ahydrogen atom, R^(5d) is a trifluoromethyl group, a pentafluoroethylgroup, a heptafluoroisopropyl group, a trifluoromethoxy group, atrifluoromethylsulfanyl group, a trifluoromethylsulfinyl group or atrifluoromethylsulfonyl group;

A compound represented by the formula (1-8) wherein A^(1d) is —NR^(7d)—or a sulfur atom, R^(7d) is a methyl group, and A^(3d) is a nitrogenatom, R^(1d) is an ethyl group, R^(2d) and R^(4d) is a hydrogen atom,R^(3d) is a chlorine atom, a bromine atom, a trifluoromethyl group or ahydrogen atom, R^(5d) is a trifluoromethyl group, a pentafluoroethylgroup, a heptafluoroisopropyl group, a trifluoromethoxy group, atrifluoromethylsulfanyl group, a trifluoromethylsulfinyl group or atrifluoromethylsulfonyl group;

A compound represented by the formula (1) wherein

A¹ is —NR⁷—, an oxygen atom or a sulfur atom,

A² is ═CR⁸—,

A³ is a nitrogen atom or ═CR⁹—,R¹ is a C1-C6 chain hydrocarbon group optionally substituted by one ormore atoms or groups selected from Group X or a C3-C6 alicyclichydrocarbon group optionally substituted by one or more atoms or groupsselected from Group Y,R², R³ and R⁴ are the same or different and each represents a C1-C6chain hydrocarbon group optionally substituted by one or more atoms orgroups selected from Group X or a hydrogen atom,R⁵ and R⁶ are the same or different and each represents a C1-C6 chainhydrocarbon group optionally substituted by one or more atoms or groupsselected from Group X, —OR¹⁰, —S(O)_(m)R¹⁰, —NR¹⁰R¹¹, —CO₂R¹⁰,—C(O)NR¹⁰R¹¹, —SF₅, a cyano group, a halogen atom or a hydrogen atom,R⁷ is a C1-C6 chain hydrocarbon group optionally substituted by one ormore atoms or groups selected from Group W, a C1-C6 chain hydrocarbongroup substituted by one 5- or 6-membered heterocyclic group (whereinthe 5- or 6-membered heterocyclic group is optionally substituted by oneor more atoms or groups selected from Group Z) or a hydrogen atom,R⁸ and R⁹ are the same or different and each represents a C1-C6 chainhydrocarbon group optionally substituted by one or more halogen atoms,—OR¹⁰, —S(O)_(m)R¹⁰, —NR¹⁰R¹¹, a cyano group, a halogen atom or ahydrogen atom,R¹⁰ and R¹¹ are the same or different and each represents a C1-C6 chainhydrocarbon group optionally substituted by one or more atoms or groupsselected from Group X, a phenyl group optionally substituted by one ormore atoms or groups selected from Group Z or a hydrogen atom,each m independently represents 0, 1 or 2, andn represents 0, 1 or 2;

The production processes of the present compound are described below.

The present compound and the intermediate compound thereof can beproduced by, for example, the following (Production process 1) to(Production process 24).

(Production Process 1)

The present compound represented by the formula (1) wherein n is 1 or 2can be produced by oxidizing the present compound wherein n is 0.

wherein the symbols are as defined in the formula (1).

The present compound represented by the formula (1-n1) wherein n is 1can be produced by oxidizing the present compound (1-n0) wherein n is 0.

The oxidation reaction is generally conducted in the presence of asolvent.

Examples of the solvent to be used in the reaction include aliphatichalogenated hydrocarbons such as dichloromethane and chloroform;alcohols such as methanol and ethanol; acetic acid; water; and mixturesthereof.

Examples of the oxidant to be used in the reaction include sodiumperiodate and m-chloroperbenzoic acid.

The amount of the oxidant to be used in the reaction is generally 1 to 3moles, preferably 1 to 1.2 moles, relative to 1 mole of the presentcompound (1-n0).

The reaction temperature of the reaction is generally within a range of−20° C. to 80° C. The reaction time of the reaction is generally withina range of 0.1 to 12 hours.

After the completion of the reaction, the present compound (1-n1) can beisolated by post-treatments, for example, extracting the reactionmixture with an organic solvent, washing the organic layer with,optionally an aqueous solution of a reduction agent (e.g., sodiumsulfite and sodium thiosulfate), followed by an aqueous solution of abase (e.g., sodium hydrogen carbonate), and then drying andconcentrating the organic layer. The isolated present compound (1-n1)can be further purified by chromatography, recrystallization, and thelike.

The present compound represented by the formula (1-n2) wherein n is 2can be produced by reacting the present compound (1-n1) wherein n is 1in the presence of an oxidant.

The reaction is generally conducted in the presence of a solvent.Examples of the solvent to be used in the reaction include aliphatichalogenated hydrocarbons such as dichloromethane and chloroform;alcohols such as methanol and ethanol; acetic acid; water; and mixturesthereof.

Examples of the oxidant to be used in the reaction includem-chloroperbenzoic acid and a hydrogen peroxide solution.

The amount of the oxidant to be used in the reaction is generally 1 to 4moles, preferably 1 to 2 moles, relative to 1 mole of the presentcompound (1-n1).

The reaction temperature of the reaction is generally within a range of−20° C. to 120° C. The reaction time of the reaction is generally withina range of 0.1 to 12 hours.

After the completion of the reaction, the present compound (1-n2) can beisolated by post-treatments, for example, extracting the reactionmixture with an organic solvent, washing the organic layer with,optionally an aqueous solution of a reduction agent (e.g., sodiumsulfite and sodium thiosulfate), followed by an aqueous solution of abase (e.g., sodium hydrogen carbonate), and then drying andconcentrating the organic layer. The isolated present compound (1-n1)can be further purified by chromatography, recrystallization, and thelike. The isolated present compound (1-n2) can be further purified bychromatography, recrystallization, and the like.

The present compound represented by the formula (1-n2) wherein n is 2can be also produced in one step (one pot) by reacting the presentcompound (1-n0) wherein n is 0 in the presence of an oxidant.

The reaction is generally conducted in the presence of a solvent.

Examples of the solvent to be used in the reaction include aliphatichalogenated hydrocarbons such as dichloromethane and chloroform;alcohols such as methanol and ethanol; acetic acid; water; and mixturesthereof.

Examples of the oxidant to be used in the reaction includem-chloroperbenzoic acid and a hydrogen peroxide solution.

The reaction may be conducted in the presence of a catalyst. Examples ofthe catalyst to be used in the reaction include sodium tungstate.

The amount of the oxidant to be used in the reaction is generally 2 to 5moles, preferably 2 to 3 moles, relative to 1 mole of the presentcompound (1-n0).

The amount of the catalyst to be used in the reaction is generally0.01-0.5 moles relative to 1 mole of the present compound (1-n0).

The reaction temperature of the reaction is generally within a range of0° C. to 120° C. The reaction time of the reaction is generally within arange of 0.1 to 12 hours.

After the completion of the reaction, the present compound (1-n2) can beisolated by post-treatments, for example, extracting the reactionmixture with an organic solvent, washing the organic layer with,optionally an aqueous solution of a reduction agent (e.g., sodiumsulfite and sodium thiosulfate), followed by an aqueous solution of abase (e.g., sodium hydrogen carbonate), and then drying andconcentrating the organic layer. The isolated present compound (1-n2)can be further purified by chromatography, recrystallization, and thelike.

(Production Process 2)

The present compound (1) can be produced by reacting the intermediatecompound (M1) with the intermediate compound (M2) or the intermediatecompound (M18) to give the intermediate compound (M3), and thencondensing the resulting intermediate compound (M3) within the molecule.

wherein the symbols are as defined in the formula (1).

The intermediate compound (M3) can be produced by reacting theintermediate compound (M1) with the intermediate compound (M2) in thepresence of a condensing agent.

The reaction is generally conducted in the presence of a solvent.Examples of the solvent to be used in the reaction include ethers suchas 1,4-dioxane, diethyl ether, tetrahydrofuran (hereinafter referred toas “THF”), and tert-butylmethyl ether; halogenated hydrocarbons such asdichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane,and chlorobenzene; aromatic hydrocarbons such as toluene, benzene, andxylene; esters such as ethyl acetate, and butyl acetate; nitriles suchas acetonitrile; aprotic polar solvents such as N,N-dimethylformamide(hereinafter referred to as “DMF”), N-methylpyrrolidone (hereinafterreferred to as “NMP”), 1,3-dimethyl-2-imidazolidinone, anddimethylsulfoxide (hereinafter referred to as “DMSO”);nitrogen-containing aromatic compounds such as pyridine and quinoline;and mixtures thereof.

Examples of the “condensing agent” to be used in the reaction includecarbodiimides such as 1-ethyl-3-(3-dimethylaminopropyl)carbodiimidehydrochloride (hereinafter referred to as “WSC”) and 1,3-dicyclohexylcarbodiimide.

The reaction may be conducted in the presence of a catalyst. Examples ofthe “catalyst” used in the reaction include 1-hydroxybenzotriazol(hereinafter referred to as “HOBt”).

The amount of the intermediate compound (M2) to be used in the reactionis generally 0.5 to 2 moles relative to 1 mole of the intermediatecompound (M1).

The amount of the condensing agent to be used in the reaction isgenerally 1 to 5 moles relative to 1 mole of the intermediate compound(M1).

The amount of the catalyst to be used in the reaction is generally 0.01to 1 moles relative to 1 mole of the intermediate compound (M1).

The reaction temperature of the reaction is generally within a range of0° C. to 120° C. The reaction time of the reaction is generally within arange of 0.1 to 24 hours.

After the completion of the reaction, the intermediate compound (M3) canbe isolated by post-treatments, for example, pouring water to thereaction mixture, extracting the reaction mixture with an organicsolvent, and concentrating the organic layer; pouring water to thereaction mixture, and collecting a solid by filtration; or collecting asolid formed in the reaction mixture by filtration. The isolatedintermediate compound (M3) can be further purified by recrystallization,chromatography, and the like.

The intermediate compound (M3) can be also produced by reacting theintermediate compound (M1) with the intermediate compound (M18).

The reaction is generally conducted in the presence of a solvent.Examples of the solvent to be used in the reaction include ethers suchas THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and1,4-dioxane; aliphatic hydrocarbons such as hexane, heptane, and octane;aromatic hydrocarbons such as toluene and xylene; halogenatedhydrocarbons such as chlorobenzene; esters such as ethyl acetate andbutyl acetate; nitriles such as acetonitrile; aprotic polar solventssuch as DMF, NMP, and DMSO; and mixtures thereof.

The reaction can be optionally conducted in the presence of a base.Examples of the base include alkali metal carbonates such as sodiumcarbonate and potassium carbonate; tertiary amines such as triethylamineand N,N-diisopropylethylamine; and nitrogen-containing aromaticcompounds such as pyridine and 4-dimethylaminopyridine.

The amount of the intermediate compound (M18) to be used in the reactionis generally 1 to 3 moles relative to 1 mole of the intermediatecompound (M1).

The reaction temperature of the reaction is generally within a range of−20° C. to 100° C. The reaction time of the reaction is generally withina range of 0.1 to 24 hours.

After the completion of the reaction, the intermediate compound (M3) canbe isolated by post-treatments, for example, pouring water to thereaction mixture, extracting the reaction mixture with an organicsolvent, and drying and concentrating the organic layer. The isolatedintermediate compound (M3) can be further purified by chromatography,recrystallization, and the like.

The present compound (1) can be produced by condensing the intermediatecompound (M3) within the molecule.

The reaction is generally conducted in the presence of a solvent.Examples of the solvent to be used in the reaction include ethers suchas 1,4-dioxane, diethyl ether, THF, and tert-butylmethyl ether;halogenated hydrocarbons such as dichloromethane, chloroform, carbontetrachloride, 1,2-dichloroethane, and chlorobenzene; aromatichydrocarbons such as toluene, benzene, and xylene; esters such as ethylacetate, and butyl acetate; nitriles such as acetonitrile; aprotic polarsolvents such as DMF, NMP, 1,3-dimethyl-2-imidazolidinone, and DMSO;nitrogen-containing aromatic compounds such as pyridine and quinoline;and mixtures thereof.

The reaction may be conducted in the presence of a condensing agent, anacid, a base or a chlorinating agent.

Examples of the condensing agent to be used in the reaction includeacetic acid anhydride, trifluoroacetic acid anhydride, WSC, a mixture oftriphenyl phosphine, a base, and carbon tetrachloride or carbontetrabromide, a mixture of triphenyl phosphine and azodiesters such asdiethyl azodicarboxylate.

Examples of the acid to be used in the reaction include sulfonic acidssuch as para-toluenesulfonic acid; carboxylic acids such as acetic acid;polyphosphoric acid; and the like.

Examples of the base to be used in the reaction includenitrogen-containing heterocyclic compounds such as pyridine, picoline,2,6-lutidine, 1,8-diazabicyclo[5.4.0]-7-undecene (hereinafter referredto as “DBU”), and 1,5-diazabicyclo[4.3.0]-5-nonene; tertiary amines suchas triethylamine and N,N-diisopropylethylamine; inorganic bases such astripotassium phosphate, potassium carbonate, and sodium hydride.

Examples of the chlorinating agent to be used in the reaction includephosphorous oxychloride; and the like.

When a condensing agent is used in the reaction, the amount of thecondensing agent is generally 1 to 5 moles relative to 1 mole of theintermediate compound (M3).

When an acid is used in the reaction, the amount of the acid isgenerally 0.1 to 5 moles relative to 1 mole of the intermediate compound(M3).

When a base is used in the reaction, the amount of the base is generally1 to 5 moles relative to 1 mole of the intermediate compound (M3).

When a chlorinating agent is used in the reaction, the amount of thechlorinating agent is generally 1 to 5 moles relative to 1 mole of theintermediate compound (M3).

The reaction temperature of the reaction is generally within a range of0° C. to 200° C. The reaction time of the reaction is generally within arange of 0.1 to 24 hours.

After the completion of the reaction, the present compound (1) can beisolated by post-treatments, for example, pouring water to the reactionmixture, extracting the reaction mixture with an organic solvent, andconcentrating the organic layer; pouring water to the reaction mixture,and collecting a solid by filtration; or collecting a solid formed inthe reaction mixture by filtration. The isolated present compound (1)can be further purified by recrystallization, chromatography, and thelike.

The present compound (1) can be also produced in one step (one pot) byreacting the intermediate compound (M1) with the intermediate compound(M2) in the presence of a condensing agent.

The reaction is generally conducted in the presence of a solvent.Examples of the solvent to be used in the reaction include ethers suchas 1,4-dioxane, diethyl ether, THF, and tert-butylmethyl ether;halogenated hydrocarbons such as dichloromethane, chloroform, carbontetrachloride, 1,2-dichloro ethane, and chlorobenzene; aromatichydrocarbons such as toluene, benzene, and xylene; esters such as ethylacetate and butyl acetate; nitriles such as acetonitrile; aprotic polarsolvents such as DMF, NMP, 1,3-dimethyl-2-imidazolidinone, and DMSO;nitrogen-containing aromatic compounds such as pyridine and quinoline;and mixtures thereof.

Examples of the condensing agent to be used in the reaction includecarbodiimides such as WSC and 1,3-dicyclohexyl carbodiimide.

The reaction may be conducted in the presence of a catalyst. Examples ofthe catalyst to be used in the reaction include 1-hydroxybenzotriazol.

The amount of the intermediate compound (M2) to be used in the reactionis generally 0.5 to 2 moles relative to 1 mole of the intermediatecompound (M1).

The amount of the condensing agent to be used in the reaction isgenerally 1 to 5 moles relative to 1 mole of the intermediate compound(M1).

The amount of the catalyst to be used in the reaction is generally 0.01to 1 moles relative to 1 mole of the intermediate compound (M1).

The reaction temperature of the reaction is generally within a range of0° C. to 200° C. The reaction time of the reaction is generally within arange of 0.1 to 24 hours.

After the completion of the reaction, the present compound (1) can beisolated by post-treatments, for example, pouring water to the reactionmixture, extracting the reaction mixture with an organic solvent, andconcentrating the organic layer; pouring water to the reaction mixture,and collecting a solid by filtration; or collecting a solid formed inthe reaction mixture by filtration. The isolated present compound (1)can be further purified by recrystallization, chromatography, and thelike.

The present compound (1) can be also produced in one step (one pot) byreacting the intermediate compound (M1) with the intermediate compound(M18).

The reaction is generally conducted in the presence or absence of asolvent.

Examples of the solvent to be used in the reaction include ethers suchas THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and1,4-dioxane; aliphatic hydrocarbons such as hexane, heptane, and octane;aromatic hydrocarbons such as toluene and xylene; halogenatedhydrocarbons such as chlorobenzene; esters such as ethyl acetate andbutyl acetate; nitriles such as acetonitrile; aprotic polar solventssuch as DMF, NMP, and DMSO; and mixtures thereof.

The reaction may be conducted in the presence of a base. Examples of thebase to be used in the reaction include alkali metal carbonates such assodium carbonate and potassium carbonate; tertiary amines such astriethylamine and N,N-diisopropylethylamine; nitrogen-containingaromatic compounds such as pyridine and 4-dimethylaminopyridine; and thelike.

The amount of the intermediate compound (M18) to be used; in thereaction is generally 1 to 3 moles relative to 1 mole of theintermediate compound (M1).

The amount of the base to be used in the reaction is generally 1 to 10moles relative to 1 mole of the intermediate compound (M1).

The reaction temperature of the reaction is generally within a range of20° C. to 200° C. The reaction time of the reaction is generally withina range of 0.1 to 24 hours.

After the completion of the reaction, the present compound (1) can beisolated by post-treatments, for example, pouring water to the reactionmixture, extracting the reaction mixture with an organic solvent, anddrying and concentrating the organic layer. The isolated presentcompound (1) can be further purified by chromatography,recrystallization, and the like.

(Production Process 3)

The present compound (P20) represented by the formula (1) wherein A¹ isa sulfur atom, and A³ is a nitrogen atom can be produced by reacting theintermediate compound (M9) with the intermediate compound (M2) or theintermediate compound (M18) to give the intermediate compound (M14), andthen reacting the resulting intermediate compound (M14) with a sulfatingagent.

wherein the symbols are as defined in the formula (1).

The intermediate compound (M14) can be produced by reacting theintermediate compound (M9) with the intermediate compound (M2).

The reaction is generally conducted in the presence or absence of asolvent.

Examples of the solvent to be used in the reaction include ethers suchas THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and1,4-dioxane; aliphatic hydrocarbons such as hexane, heptane, and octane;aromatic hydrocarbons such as toluene and xylene; halogenatedhydrocarbons such as chlorobenzene; esters such as ethyl acetate andbutyl acetate; nitriles such as acetonitrile; aprotic polar solventssuch as DMF, NMP, and DMSO; nitrogen-containing aromatic compounds suchas pyridine and quinoline; and mixtures thereof.

Examples of the dehydrating condensing agent to be used in the reactioninclude carbodiimides such as WSC, 1,3-dicyclohexylcarbodiimide, and BOPagents.

The amount of the intermediate compound (M2) to be used in the reactionis generally 1 to 3 moles relative to 1 mole of the intermediatecompound (M9).

The amount of the dehydrating condensing agent to be used in thereaction is generally 1 to 5 moles relative to 1 mole of theintermediate compound (M9).

The reaction temperature of the reaction is generally within a range of0° C. to 200° C. The reaction time of the reaction is generally within arange of 0.1 to 24 hours.

After the completion of the reaction, the intermediate compound (M14)can be isolated by post-treatments, for example, pouring water to thereaction mixture, extracting the reaction mixture with an organicsolvent, and drying and concentrating the organic layer. The isolatedintermediate compound (M14) can be further purified by chromatography,recrystallization, and the like.

The intermediate compound (M14) can be also produced by reacting theintermediate compound (M9) with the intermediate compound (M18).

The reaction is generally conducted in the presence or absence of asolvent, and may be conducted in the presence of a base.

Examples of the solvent to be used in the reaction include ethers suchas THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and1,4-dioxane; aliphatic hydrocarbons such as hexane, heptane, and octane;aromatic hydrocarbons such as toluene and xylene; halogenatedhydrocarbons such as chlorobenzene; esters such as ethyl acetate andbutyl acetate; nitriles such as acetonitrile; aprotic polar solventssuch as DMF, NMP, and DMSO; nitrogen-containing aromatic compounds suchas pyridine and quinoline; and mixtures thereof.

Examples of the base to be used in the reaction include alkali metalcarbonates such as sodium carbonate and potassium carbonate; tertiaryamines such as triethylamine and N,N-diisopropylethylamine;nitrogen-containing aromatic compounds such as pyridine and4-dimethylaminopyridine; and the like.

The amount of the intermediate compound (M18) to be used in the reactionis generally 1 to 3 moles relative to 1 mole of the intermediatecompound (M9).

The amount of the base to be used in the reaction is generally 1 to 5moles relative to 1 mole of the intermediate compound (M9).

The reaction temperature of the reaction is generally within a range of0° C. to 200° C. The reaction time of the reaction is generally within arange of 0.1 to 24 hours.

After the completion of the reaction, the intermediate compound (M14)can be isolated by post-treatments, for example, pouring water to thereaction mixture, extracting the reaction mixture with an organicsolvent, and drying and concentrating the organic layer. The isolatedintermediate compound (M14) can be further purified by chromatography,recrystallization, and the like.

The present compound (P20) can be produced by reacting the intermediatecompound (M14) with a sulfating agent.

The reaction is generally conducted in the presence or absence of asolvent. Examples of the solvent to be used in the reaction includeethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran,tert-butylmethyl ether, and diglyme; halogenated hydrocarbons such asdichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane,and chlorobenzene; aromatic hydrocarbons such as toluene, benzene, andxylene; nitriles such as acetonitrile; nitrogen-containing aromaticcompounds such as pyridine, picoline, lutidine, and quinoline; andmixtures thereof.

Examples of the sulfating agent to be used in the reaction includephosphorus pentasulfide, Lawesson's reagent(2,4-bis-(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide);and the like.

The amount of the sulfating agent to be used in the reaction isgenerally 1 to 3 moles relative to 1 mole of the intermediate compound(M14).

The reaction temperature of the reaction is generally within a range of0° C. to 200° C. The reaction time of the reaction is generally within arange of 1 to 24 hours.

After the completion of the reaction, the present compound (P20) can beisolated by post-treatments, for example, pouring water to the reactionmixture, extracting the reaction mixture with an organic solvent, andconcentrating the organic layer; pouring water to the reaction mixture,and collecting a solid by filtration; or collecting a solid formed inthe reaction mixture by filtration. The isolated present compound (P20)can be further purified by recrystallization, chromatography, and thelike.

(Production Process 4)

The present compound (1) can be produced by reacting the intermediatecompound (M1) with the intermediate compound (M4) in the presence of anoxidant.

wherein the symbols are as defined in the formula (1).

The reaction is generally conducted in the presence of a solvent.Examples of the solvent to be used in the reaction include alcohols suchas methanol and ethanol; ethers such as 1,4-dioxane, diethyl ether, THF,and tert-butylmethyl ether; halogenated hydrocarbons such asdichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane,and chlorobenzene; aromatic hydrocarbons such as toluene, benzene, andxylene; esters such as ethyl acetate and butyl acetate; nitriles such asacetonitrile; aprotic polar solvents such as DMF, NMP,1,3-dimethyl-2-imidazolidinone, and DMSO; nitrogen-containing aromaticcompounds such as pyridine and quinoline; and mixtures thereof.

The reaction may be conducted in the presence of an acid. Examples ofthe acid to be used in the reaction include sulfonic acids such aspara-toluenesulfonic acid; carboxylic acids such as acetic acid;polyphosphoric acid; and the like.

The reaction may be conducted in the presence of a sulfite. Examples ofthe sulfite to be used in the reaction include sodium hydrogen sulfite,and disodium sulfite.

Examples of the oxidant to be used in the reaction include oxygen,copper (II) chloride, DDQ; and the like.

The amount of the intermediate compound (M4) to be used in the reactionis generally 1 to 2 moles relative to 1 mole of the intermediatecompound (M1).

The amount of the acid to be used in the reaction is generally 0.1 to 2moles relative to 1 mole of the intermediate compound (M1).

The amount of the sulfite to be used in the reaction is generally 1 to 5moles relative to 1 mole of the intermediate compound (M1).

The amount of the oxidant to be used in the reaction is generally 1 to 5moles relative to 1 mole of the intermediate compound (M1).

The reaction temperature of the reaction is generally within a range of0° C. to 200° C. The reaction time of the reaction is generally within arange of 0.1 to 24 hours.

After the completion of the reaction, the present compound (1) can beisolated by post-treatments, for example, pouring water to the reactionmixture, extracting the reaction mixture with an organic solvent, andconcentrating the organic layer; pouring water to the reaction mixture,and collecting a solid by filtration; or collecting a solid formed inthe reaction mixture by filtration. The isolated present compound (1)can be further purified by recrystallization, chromatography, and thelike.

(Production Process 5)

The present compound represented by the formula (1) wherein n is 0 canbe produced by reacting the intermediate compound (M6) with theintermediate compound (M7) in the presence of a base.

wherein V² represents a halogen atom, and the other symbols are asdefined in the formula (1).

The reaction is generally conducted in the presence of a solvent.

Examples of the solvent to be used in the reaction include ethers suchas THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and1,4-dioxane; aromatic hydrocarbons such as toluene and xylene; nitrilessuch as acetonitrile; aprotic polar solvents such as DMF, NMP, and DMSO;water; and mixtures thereof.

Examples of the base to be used in the reaction include alkali metalcarbonates such as sodium carbonate and potassium carbonate; and alkalimetal hydrides such as sodium hydride.

The amount of the intermediate compound (M7) to be used in the reactionis generally 1 to 10 moles relative to 1 mole of the intermediatecompound (M6).

The amount of the base to be used in the reaction is generally 1 to 10moles relative to 1 mole of the intermediate compound (M6).

The reaction temperature of the reaction is generally within a range of0° C. to 150° C. The reaction time of the reaction is generally within arange of 0.5 to 24 hours.

After the completion of the reaction, the present compound (1) wherein nis 0 can be isolated by post-treatments, for example, extracting thereaction mixture with an organic solvent, and drying and concentratingthe organic layer. The isolated present compound (1) wherein n is 0 canbe further purified by chromatography, recrystallization, and the like.

In reaction, V² is preferably a fluorine atom or a chlorine atom.

(Production Process 6)

The intermediate compound (M6) can be produced by reacting theintermediate compound (M1) with the intermediate compound (M19) or theintermediate compound (M39) to give the intermediate compound (M20), andthen condensing the resulting intermediate compound (M20) within themolecule.

wherein V² represents a halogen atom, and the other symbols are asdefined in the formula (1).

The intermediate compound (M20) can be produced in the same manner as inProduction process 2 except for using the intermediate compound (M19)instead of the intermediate compound (M2).

The intermediate compound (M20) can be produced in the same manner as inProduction process 2 except for using the intermediate compound (M39)instead of the intermediate compound (M18).

The intermediate compound (M6) can be produced in the same manner as inProduction process 2 except for using the intermediate compound (M20)instead of the intermediate compound (M3).

The intermediate compound (M6) can be produced in one step (one pot) inthe same manner as in Production process 2 except for using theintermediate compound (M19) instead of the intermediate compound (M6.)The intermediate compound (M6) can be produced in one step (one pot) inthe same manner as in Production process 2 except for using theintermediate compound (M39) instead of the intermediate compound (M2).

In reaction, V² is preferably a fluorine atom or a chlorine atom.

(Production Process 7)

The intermediate compound represented by the formula (M3) wherein n is 0can be produced by reacting the intermediate compound (M20) with theintermediate compound (M7).

The present compound represented by the formula (1) wherein n is 0 canbe produced by condensing the resulting intermediate compound (M3)within the molecule.

wherein V² represents a halogen atom, and the other symbols are asdefined in the formula (1).

The intermediate compound represented by the formula (M3) wherein n is 0can be produced in the same manner as in Production process 5 except forusing the intermediate compound (M20) instead of the intermediatecompound (M6).

The present compound represented by the formula (1) wherein n is 0 canbe produced in the same manner as in Production process 2 except forusing the intermediate compound represented by the formula (M3) whereinn is 0 instead of the intermediate compound (M3).

The present compound represented by the formula (1) wherein n is 0 canbe produced in one step (one pot) in the same manner as in Productionprocess 5 except for using the intermediate compound (M20) instead ofthe intermediate compound (M6).

In reaction, V² is preferably a fluorine atom or a chlorine atom.

(Production Process 8)

The present compound represented by the formula (1) wherein n is 0 canbe produced by reacting the intermediate compound (M8) or a disulfidethereof, the intermediate compound (M8′), with the intermediate compound(M17) in the presence of a base.

wherein L is a leaving group such as a chlorine atom, a bromine atom, aniodine atom, a trifluoromethanesulfonyloxy group and amethanesulfonyloxy group, and the other symbols are as defined in theformula (1).

The reaction is generally conducted in the presence of a solvent.

Examples of the solvent to be used in the reaction include ethers suchas THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and1,4-dioxane; aromatic hydrocarbons such as toluene and xylene; nitrilessuch as acetonitrile; aprotic polar solvents such as DMF, NMP, and DMSO;and mixtures thereof.

Examples of the base to be used in the reaction include inorganic basessuch as alkali metal or alkaline earth metal hydrides, e.g., sodiumhydride, potassium hydride, and calcium hydride; sodium carbonate; andpotassium carbonate; and organic base such as triethylamine.

When the intermediate compound (M8′), which is a sulfide, is used, thereaction is generally conducted in the presence of a reductant.

Examples of the reductant to be used in the reaction include sodiumhydroxymethanesulfinate (trade name: Rongalite).

The amount of the intermediate compound (M17) to be used in the reactionis generally 1 to 10 moles relative to 1 mole of the intermediatecompound (M8).

The amount of the base to be used in the reaction is generally 1 to 10moles relative to 1 mole of the intermediate compound (M8).

When the intermediate compound (M8′), which is a disulfide, is used, theamount of the intermediate compound (M17) to be used in the reaction isgenerally 2 to 10 moles relative to 1 mole of the intermediate compound(M8′). The amount of the base to be used in the reaction is generally 2to 10 moles relative to 1 mole of the intermediate compound (M8′). Theamount of the reductant to be used in the reaction is generally 1 to 5moles relative to 1 mole of the intermediate compound (M8′).

The reaction temperature of the reaction is generally within a range of0° C. to 100° C. The reaction time of the reaction is generally within arange of 0.1 to 24 hours.

After the completion of the reaction, the present compound (1) wherein nis 0 can be isolated by post-treatments, for example, extracting thereaction mixture with an organic solvent, and drying and concentratingthe organic layer. The isolated present compound (1) wherein n is 0 canbe further purified by chromatography, recrystallization, and the like.

(Production Process 9)

The present compound represented by the formula (1) wherein n is 0 canbe produced by reacting the intermediate compound (M8′) with theintermediate compound (M17′-1) or the intermediate compound (M17′-2)

wherein V³ is a chlorine atom, a bromine atom, or an iodine atom, andthe other symbols are as defined in the formula (1).

The reaction is generally conducted in the presence of a solvent.

Examples of the solvent to be used in the reaction include ethers suchas THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and1,4-dioxane; aromatic hydrocarbons such as toluene and xylene; nitrilessuch as acetonitrile; aprotic polar solvents such as DMF, NMP, and DMSO;and mixtures thereof.

The amount of the intermediate compound (M17′-1) to be used in thereaction is generally 1 to 2 moles relative to 1 mole of theintermediate compound (M8′).

When the intermediate compound (M17′-2) is used, the intermediatecompound (M17′-2) is generally used in an amount of 1 to 2 molesrelative to 1 mole of the intermediate compound (M8′).

The reaction temperature of the reaction is generally within a range of−80° C. to 100° C. The reaction time of the reaction is generally withina range of 0.1 to 24 hours.

After the completion of the reaction, the present compound (1) wherein nis 0 can be isolated by post-treatments, for example, extracting thereaction mixture with an organic solvent, and drying and concentratingthe organic layer. The isolated present compound (1) wherein n is 0 canbe further purified by chromatography, recrystallization, and the like.

(Production Process 10)

The intermediate compound (M8) can be produced by reacting theintermediate compound (M6) with a sulfating agent. The intermediatecompound (M8′), which is a disulfide of the intermediate compound (M8),can be produced by oxidizing the intermediate compound (M8).

wherein V² represents a halogen atom, and the other symbols are asdefined in the formula (1).

The intermediate compound (M8) can be produced in the same manner as inProduction process 5 except for using sodium sulfide, sodium hydrogensulfide, hydrogen sulfide or the like instead of the intermediatecompound (M7).

In this case, the reaction from the intermediate compound (M8) to theintermediate compound (M8′) is easily progressed, and thus theintermediate compound (M8′) may be produced in the synthesis of theintermediate compound (M8).

In reaction, V² is preferably a fluorine atom or a chlorine atom.

The intermediate compound (M8′) can be produced by reacting theintermediate compound (M8) with an oxidant.

The reaction is generally conducted in the presence of a solvent.

Examples of the solvent to be used in the reaction include water;alcohols such as methanol and ethanol; ethers such as THF, ethyleneglycol dimethyl ether, tert-butylmethyl ether, and 1,4-dioxane; aromatichydrocarbons such as toluene and xylene; nitriles such as acetonitrile;aprotic polar solvents such as DMF, NMP, and DMSO; carboxylic acids suchas acetic acid; and mixtures thereof.

Examples of the oxidant to be used in the reaction include oxygen,iodine, hydrogen peroxide solution, potassium ferricyanide; and thelike.

The amount of the oxidant to be used in the reaction is generally 0.5 to10 moles relative to 1 mole of the intermediate compound (M8).

The reaction temperature of the reaction is generally within a range of0° C. to 100° C. The reaction time of the reaction is generally within arange of 0.1 to 24 hours.

After the completion of the reaction, the intermediate compound (M8′)can be isolated by post-treatments, for example, extracting the reactionmixture with an organic solvent, and drying and concentrating theorganic layer. The isolated intermediate compound (M8′) can be furtherpurified by chromatography, recrystallization, and the like.

(Production Process 11)

The present compound (P3) represented by the formula (1) wherein A¹ is—NR⁷′— can be produced by reacting the present compound (P2) representedby the formula (1) wherein A¹ is —NH— with the intermediate compound(M10) in the presence of a base.

wherein R⁷′ is any of the groups for R⁷ other than a hydrogen atom inthe formula (1), L is an leaving group such as a chlorine atom, abromine atom, an iodine atom, a trifluoromethanesulfonyloxy group and amethanesulfonyloxy group, and the other symbols are as defined in theformula (1).

The reaction is generally conducted in the presence of a solvent.

Examples of the solvent to be used in the reaction include ethers suchas THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and1,4-dioxane; aromatic hydrocarbons such as toluene and xylene; nitrilessuch as acetonitrile; aprotic polar solvents such as DMF, NMP, and DMSO;and mixtures thereof.

Examples of the base to be used in the reaction include alkali metal oralkaline earth metal hydride such as sodium hydride, potassium hydride,and calcium hydride; inorganic bases such as sodium carbonate, andpotassium carbonate; organic bases such as triethylamine; and the like.

The amount of the intermediate compound (M10) to be used in the reactionis generally 1 to 5 moles relative to 1 mole of the present compound(P2).

The amount of the base to be used in the reaction is generally 1 to 3moles relative to 1 mole of the present compound (P2).

The reaction temperature of the reaction is generally within a range of0° C. to 100° C. The reaction time of the reaction is generally within arange of 0.1 to 24 hours.

After the completion of the reaction, the present compound (P3) can beisolated by post-treatments, for example, extracting the reactionmixture with an organic solvent, and drying and concentrating theorganic layer. The isolated present compound (P3) can be furtherpurified by chromatography, recrystallization, and the like.

(Production Process 12)

The intermediate compound (M2) can be produced by hydrolyzing theintermediate compound (M37)

wherein the symbols are as defined in the formula (1).

When the hydrolysis is conducted by using an acid, an aqueous solutionof the acid is generally used as a solvent in the reaction.

Examples of the acid to be used in the reaction include mineral acidssuch as hydrochloric acid, nitric acid, phosphoric acid, and sulfuricacid; and carboxylic acids such as acetic acid and trifluoroacetic acid.

The reaction temperature of the reaction is generally within a range of0° C. to 100° C. The reaction time of the reaction is generally within arange of 0.1 to 24 hours.

After the completion of the reaction, the intermediate compound (M2) canbe isolated by post-treatments, for example, extracting the reactionmixture with an organic solvent, and drying and concentrating theorganic layer. The isolated intermediate compound (M2) can be furtherpurified by chromatography, recrystallization, and the like.

When the hydrolysis is conducted by using a base, the reaction isgenerally conducted in the presence of a solvent.

Examples of the solvent to be used in the reaction include ethers suchas THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and1,4-dioxane; alcohols such as methanol and ethanol; water; and mixturesthereof.

Examples of the base to be used in the reaction include alkali metalhydroxides such as sodium hydroxide and potassium hydroxide.

The amount of the base to be used in the reaction is generally 1 to 10moles relative to 1 mole of the intermediate compound (M37).

The reaction temperature of the reaction is generally within a range of0° C. to 120° C. The reaction time of the reaction is generally within arange of 0.1 to 24 hours.

After the completion of the reaction, the intermediate compound (M2) canbe isolated by post-treatments, for example, acidifying the reactionsolution, extracting the reaction mixture with an organic solvent, anddrying and concentrating the organic layer. The isolated intermediatecompound (M2) can be further purified by chromatography,recrystallization, and the like.

(Production Process 13)

The intermediate compound (M18) can be produced by reacting theintermediate compound (M2) with a chlorinating agent.

wherein the symbols are as defined in the formula (1).

The reaction is generally conducted in the presence of a solvent.

Examples of the solvent to be used in the reaction include ethers suchas THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and1,4-dioxane; aromatic hydrocarbons such as toluene and xylene; aliphatichalogenated hydrocarbons such as dichloromethane and chloroform; andmixtures thereof.

Examples of the chlorinating agent to be used in the reaction includethionyl chloride, oxalyl dichloride, phosphorous oxychloride; and thelike.

The amount of the chlorinating agent to be used in the reaction isgenerally 1 to 5 moles relative to 1 mole of the intermediate compound(M2).

The reaction temperature of the reaction is generally within a range of0° C. to 0.100° C. The reaction time of the reaction is generally withina range of 0.1 to 24 hours.

After the completion of the reaction, the intermediate compound (M18)can be isolated by removing the solvent from the reaction mixture.

(Production Process 14)

The intermediate compound (M2), the intermediate compound (M4) or theintermediate compound (M37) can be produced by reacting the intermediatecompound (M7) with the intermediate compound (M19), the intermediatecompound (M22) or the intermediate compound (M36), respectively, andoptionally oxidizing the resulting compound.

wherein V² represents a halogen atom, and the other symbols are asdefined in the formula (1).

The intermediate compound (M2) wherein n is 0 can be produced in thesame manner as in Production process 5 except for using the intermediatecompound (M19) instead of the intermediate compound (M6).

The intermediate compound (M4) wherein n is 0 can be produced in thesame manner as in Production process 5 except for using the intermediatecompound (M22) instead of the intermediate compound (M6).

The intermediate compound (M37) wherein n is 0 can be produced in thesame manner as in Production process 5 except for using the intermediatecompound (M36) instead of the intermediate compound (M6).

The intermediate compound (M2) wherein n is 1 or 2 can be produced inthe same manner as in Production process 1 except for using theintermediate compound (M2) wherein n is 0 instead of the presentcompound (1) wherein n is 0.

The intermediate compound (M4) wherein n is 1 or 2 can be produced inthe same manner as in Production process 1 except for using theintermediate compound (M4) wherein n is 0 instead of the presentcompound (1) wherein n is 0.

The intermediate compound (M37) wherein n is 1 or 2 can be produced inthe same manner as in Production process 1 except for using theintermediate compound (M37) wherein n is 0 instead of the presentcompound (1) wherein n is 0.

In reaction, V² is preferably a fluorine atom or a chlorine atom.

(Production Process 15)

The intermediate compound (M30) can be produced by nitrating theintermediate compound (M29), or reacting the intermediate compound (M33)with the intermediate compound (M28). By reducing the resultingintermediate compound (M30), the intermediate compound (M1) representedby the formula (M1) wherein A¹ is —NR⁷— can be produced.

wherein the symbols are as defined in the formula (1).

The intermediate compound (M30) can be produced by reacting theintermediate compound (M33) with the intermediate compound (M28) in thepresence of a base.

The reaction is generally conducted in the presence of a solvent.

Examples of the solvent to be used in the reaction include ethers suchas THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and1,4-dioxane; aromatic hydrocarbons such as toluene and xylene; nitrilessuch as acetonitrile; aprotic polar solvents such as DMF, NMP, and DMSO;and mixtures thereof.

The reaction may be conducted in the presence of a base.

Examples of the base to be used in the reaction include alkali metalhydrides such as sodium hydride; alkali metal carbonates such as sodiumcarbonate and potassium carbonate; tertiary amines such as triethylamineand N,N-diisopropylethylamine; and nitrogen-containing aromaticcompounds such as pyridine and 4-dimethylaminopyridine.

The amount of the intermediate compound (M28) to be used in the reactionis generally 1 to 10 moles relative to 1 mole of the intermediatecompound (M33).

The amount of the base to be used in the reaction is generally 0 to 10moles relative to 1 mole of the intermediate compound (M6).

The reaction temperature of the reaction is generally within a range of0° C. to 150° C. The reaction time of the reaction is generally within arange of 0.5 to 24 hours.

After the completion of the reaction, the intermediate compound (M30)can be isolated by post-treatments, for example, extracting the reactionmixture with an organic solvent, and drying and concentrating theorganic layer. The isolated intermediate compound (M30) can be furtherpurified by chromatography, recrystallization, and the like.

The intermediate compound (M30) can be produced by reacting theintermediate compound (M29) with a nitrating agent.

The reaction is generally conducted in the presence of a solvent.Examples of the solvent to be used in the reaction include aliphatichalogenated hydrocarbons such as dichloromethane, and chloroform; aceticacid, concentrated sulfuric acid, concentrated nitric acid, water; andmixtures thereof.

Examples of the nitrating agent to be used in the reaction includeconcentrated nitric acid; and the like.

The amount of the nitrating agent to be used in the reaction isgenerally 1 to 3 moles relative to 1 mole of the intermediate compound(M29).

The reaction temperature of the reaction is generally within a range of−10° C. to 100° C. The reaction time of the reaction is generally withina range of 0.1 to 24 hours.

After the completion of the reaction, the intermediate compound (M30)can be isolated by post-treatments, for example, pouring water to thereaction mixture, extracting the reaction mixture with an organicsolvent, and drying and concentrating the organic layer. The isolatedintermediate compound (M30) can be further purified by chromatography,recrystallization, and the like.

The intermediate compound (M30) wherein R⁷ is a group other than ahydrogen atom can be produced in the same manner as in Productionprocess 11 except for using the intermediate compound (M30) wherein R⁷is a hydrogen atom instead of the present compound (P2).

The intermediate compound (M1) wherein A¹ is —NR⁷— can be produced byreacting the intermediate compound (M30) with hydrogen in the presenceof a hydrogenating catalyst.

The reaction is generally conducted in the presence of a solvent underhydrogen atmosphere at 1 to 100 atm.

Examples of the solvent to be used in the reaction include ethers suchas THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and1,4-dioxane; esters such as ethyl acetate and butyl acetate; alcoholssuch as methanol and ethanol; water; and mixtures thereof.

Examples of the hydrogenating catalyst to be used in the reactioninclude transition metal compounds such as palladium carbon, palladiumhydroxide, Raney nickel, and platinum oxide.

The amount of the hydrogen to be used in the reaction is generally 3moles relative to 1 mole of the intermediate compound (M30).

The amount of the hydrogenating catalyst to be used in the reaction isgenerally 0.001 to 0.5 moles relative to 1 mole of the intermediatecompound (M30).

The reaction may be conducted in the presence of an acid or a base, ifnecessary.

Examples of the acid to be used in the reaction include acetic acid,hydrochloric acid, and the like.

Examples of the base to be used in the reaction include tertiary aminessuch as triethylamine; magnesium oxide; and the like.

The reaction temperature of the reaction is generally within a range of−20° C. to 100° C. The reaction time of the reaction is generally withina range of 0.1 to 24 hours.

After the completion of the reaction, the intermediate compound (M1)wherein A¹ is —NR⁷— can be isolated by post-treatments, for example,filtrating the reaction mixture, optionally extracting the reactionmixture with an organic solvent, and drying and concentrating theorganic layer. The isolated intermediate compound (M1) wherein A¹ is—NR⁷— can be further purified by chromatography, recrystallization, andthe like.

As shown below, the intermediate compound (M30) can be produced byacetylating the intermediate compound (M29) to give the intermediatecompound (M29′), nitrating the resulting intermediate compound (M29′) togive the intermediate compound (M30′), and hydrolyzing the resultingintermediate compound (M30′).

wherein the symbols are as defined in the formula (1).

The intermediate compound (M29′) can be produced by reacting theintermediate compound (M29) with an acylating agent.

The reaction is generally conducted in the presence of a solvent orusing the acylating agent as a solvent.

Examples of the solvent to be used in the reaction include aliphatichalogenated hydrocarbons such as dichloromethane and chloroform; etherssuch as THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and1,4-dioxane; aromatic hydrocarbons such as toluene and xylene; nitrilessuch as acetonitrile; aprotic polar solvents such as DMF, NMP, and DMSO;and mixtures thereof.

Examples of the acylating agent to be used in the reaction includeacetic acid anhydride, para-acetoxynitrobenzene; and the like.

The reaction may be conducted in the presence of a base.

Examples of the base to be used in the reaction include tertiary aminessuch as triethylamine and N,N-diisopropylethylamine; andnitrogen-containing aromatic compounds such as pyridine and4-dimethylaminopyridine.

The amount of the acylating agent to be used in the reaction isgenerally not less than 1 mole relative to 1 mole of the intermediatecompound (M29).

The amount of the base to be used in the reaction is generally 0.1 to 10moles relative to 1 mole of the intermediate compound (M29).

The reaction temperature of the reaction is generally within a range of0° C. to 150° C. The reaction time of the reaction is generally within arange of 0.5 to 24 hours.

After the completion of the reaction, the intermediate compound (M29′)can be isolated by post-treatments, for example, extracting the reactionmixture with an organic solvent, and drying and concentrating theorganic layer. The isolated intermediate compound (M29′) can be furtherpurified by chromatography, recrystallization, and the like.

The intermediate compound (M30′) can be produced in the same manner asin Production process 15 except for using the intermediate compound(M29′) instead of the intermediate compound (M29).

The intermediate compound (M30) can be produced by hydrolyzing theintermediate compound (M30′) in the presence of an acid or a base.

When the hydrolysis is conducted by using an acid, an aqueous solutionof the acid is generally used as a solvent in the reaction.

Examples of the acid to be used in the reaction include mineral acidssuch as hydrochloric acid and sulfuric acid; and carboxylic acids suchas acetic acid and trifluoroacetic acid.

The reaction temperature of the reaction is generally within a range of0° C. to 100° C. The reaction time of the reaction is generally within arange of 0.1 to 24 hours.

After the completion of the reaction, the intermediate compound (M30)can be isolated by post-treatments, for example, extracting the reactionmixture with an organic solvent, and drying and concentrating theorganic layer. The isolated intermediate compound (M30) can be furtherpurified by chromatography, recrystallization, and the like.

When the hydrolysis is conducted by using a base, the reaction isgenerally conducted in the presence of a solvent.

Examples of the solvent to be used in the reaction include ethers suchas THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and1,4-dioxane; alcohols such as methanol and ethanol; water; and mixturesthereof.

Examples of the base to be used in the reaction include alkali metalhydroxides such as sodium hydroxide and potassium hydroxide; hydrazine;and the like.

The amount of the base to be used in the reaction is generally 1 to 10moles relative to 1 mole of the intermediate compound (M30′).

The reaction temperature of the reaction is generally within a range of0° C. to 120° C. The reaction time of the reaction is generally within arange of 0.1 to 24 hours.

After the completion of the reaction, the intermediate compound (M30)can be isolated by post-treatments, for example, acidifying the reactionsolution, extracting the reaction mixture with an organic solvent, anddrying and concentrating the organic layer. The isolated intermediatecompound (M30) can be further purified by chromatography,recrystallization, and the like.

(Production Process 16)

The intermediate compound (M1) wherein A¹ is —NR⁷— can be produced bybrominating the intermediate compound (M29) to give the intermediatecompound (M35), and aminating the resulting intermediate compound (M35).

wherein the symbols are as defined in the formula (1).

The intermediate compound (M35) can be produced by reacting theintermediate compound (M29) with a brominating agent.

The reaction is generally conducted in the presence of a solvent.

Examples of the solvent to be used in the reaction include water; aceticacid; ethers such as 1,4-dioxane, diethyl ether, and THF; esters such asethyl acetate and butyl acetate; halogenated hydrocarbons such asdichloromethane, chloroform, carbon tetrachloride, and 1,2-dichloroethane; nitriles such as acetonitrile; aprotic polar solvents such asDMF, NMP, and DMSO; and mixtures thereof.

Examples of the brominating agent to be used in the reaction includeN-bromosuccinimide, bromine, and the like.

The amount of the brominating agent to be used in the reaction isgenerally 1 to 3 moles relative to 1 mole of the intermediate compound(M29).

The reaction temperature of the reaction is generally within a range of−10° C. to 100° C. The reaction time of the reaction is generally withina range of 0.1 to 24 hours.

After the completion of the reaction, the intermediate compound (M35)can be isolated by post-treatments, for example, pouring water to thereaction mixture, extracting the reaction mixture with an organicsolvent, and concentrating the organic layer; pouring water to thereaction mixture, and collecting a solid by filtration; or collecting asolid formed in the reaction mixture by filtration. The isolatedintermediate compound (M35) can be further purified byrecrystallization, chromatography, and the like.

The intermediate compound (M1) wherein A¹ is —NR⁷— can be produced byreacting the intermediate compound (M35) with an aminating agent in thepresence of a copper compound.

The reaction is generally conducted in the presence of a solvent.Examples of the solvent to be used in the reaction include water;alcohols such as methanol and ethanol; ethers such as 1,4-dioxane,diethyl ether, and THF; esters such as ethyl acetate and butyl acetate;halogenated hydrocarbons such as dichloromethane, chloroform, carbontetrachloride, and 1,2-dichloroethane; nitriles such as acetonitrile;aprotic polar solvents such as DMF, NMP, and DMSO; nitrogen-containingaromatic compounds such as pyridine and quinoline; and mixtures thereof.

Examples of the aminating agent to be used in the reaction includeammonia, aqueous ammonia, lithium amide, and the like.

Examples of the copper compound to be used in the reaction includecopper, copper (I) iodide, copper (I) oxide, copper (II) oxide,acetylacetone copper (II), copper (II) acetate, copper (II) sulfate, andthe like.

The reaction may be conducted in the presence of a ligand. Examples ofthe ligand to be used in the reaction include acetylacetone, salen,phenanthroline, and the like.

The reaction may be conducted in the presence of a base.

Examples of the base to be used in the reaction includenitrogen-containing heterocyclic compounds such as pyridine, picoline,2,6-lutidine, DBU, and 1,5-diazabicyclo[4.3.0]-5-nonene; tertiary aminessuch as triethylamine and N,N-diisopropylethylamine; inorganic basessuch as tripotassium phosphate, potassium carbonate, cesium carbonate,and sodium hydroxide.

The amount of the aminating agent to be used in the reaction isgenerally 1 to 5 moles relative to 1 mole of the intermediate compound(M35).

The amount of the copper compound to be used in the reaction isgenerally 0.02 to 0.2 moles relative to 1 mole of the intermediatecompound (M35).

The amount of the base to be used in the reaction is generally 1 to 5moles relative to 1 mole of the intermediate compound (M35).

The reaction temperature of the reaction is generally within a range of30° C. to 200° C. The reaction time of the reaction is generally withina range of 0.1 to 48 hours.

After the completion of the reaction, the intermediate compound (M1)wherein A¹ is —NR⁷— can be isolated by post-treatments, for example,pouring water to the reaction mixture, extracting the reaction mixturewith an organic solvent, and drying and concentrating the organic layer.The isolated intermediate compound (M1) wherein A¹ is —NR⁷— can befurther purified by chromatography, recrystallization, and the like.

(Production Process 17)

The intermediate compound (M1) represented by the formula (M1) whereinA¹ is an oxygen atom can be produced by nitrating the intermediatecompound (M31), to give the intermediate compound (M32), and reducingthe resulting intermediate compound (M32).

wherein the symbols are as defined in the formula (1).

The intermediate compound (M32) can be produced in the same manner as inProduction process 15 except for using the intermediate compound (M31)instead of the intermediate compound (M29).

The intermediate compound (M1) wherein A¹ is an oxygen atom can beproduced in the same manner as in Production process 15 except for usingthe intermediate compound (M32) instead of the intermediate compound(M30).

(Production Process 18)

The intermediate compound (M1) represented by the formula (M1) whereinA¹ is a sulfur atom can be produced by reacting the intermediatecompound (M33) with a sulfating agent to give the intermediate compound(M34), and reducing the resulting intermediate compound (M34).

wherein the symbols are as defined in the formula (1).

The intermediate compound (M34) can be produced by reacting theintermediate compound (M33) with thiourea in the presence of a base.

The reaction is generally conducted in the presence of a solvent.Examples of the solvent to be used in the reaction include alcohols suchas methanol and ethanol; water; and mixtures thereof.

Examples of the base to be used in the reaction include alkali metalhydroxide such as sodium hydroxide and potassium hydroxide.

The amount of the thiourea to be used in the reaction is generally 0.5to 3 moles relative to 1 mole of the intermediate compound (M33).

The amount of the base to be used in the reaction is generally 1 to 10moles relative to 1 mole of the intermediate compound (M33).

The reaction temperature of the reaction is generally within a range of0° C. to 100° C. The reaction time of the reaction is generally within arange of 0.1 to 24 hours.

After the completion of the reaction, the intermediate compound (M34)can be isolated by post-treatments, for example, adding an acid to thereaction mixture, extracting the reaction mixture with an organicsolvent, and drying and concentrating the organic layer. The isolatedintermediate compound (M34) can be further purified by chromatography,recrystallization, and the like.

The intermediate compound (M1) wherein A¹ is a sulfur atom can beproduced by reacting the intermediate compound (M34) with a reductant.

The reduction reaction may be conducted in the presence of, for example,metal powder such as iron powder, and zinc powder; acids such ashydrochloric acid and acetic acid; and water.

The reaction is generally conducted in the presence of a solvent.Examples of the solvent to be used in the reaction include ethers suchas THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and1,4-dioxane; esters such as ethyl acetate and butyl acetate; alcoholssuch as methanol and ethanol; aprotic polar solvents such as DMF, NMP,and DMSO; and mixtures thereof.

Examples of the reductant to be used in the reaction include metalpowders such as iron powders, zinc powders and tin dichloride powders.

The amount of the metal powder to be used in the reaction is generally 3to 10 moles relative to 1 mole of the intermediate compound (M34).

The reaction temperature of the reaction is generally within a range of0° C. to 100° C. The reaction time of the reaction is generally within arange of 0.1 to 24 hours.

After the completion of the reaction, the intermediate compound (M1)wherein A¹ is a sulfur atom can be isolated by post-treatments, forexample, pouring water to the reaction mixture, extracting the reactionmixture with an organic solvent, and drying and concentrating theorganic layer. The isolated intermediate compound (M1) wherein A¹ is asulfur atom can be further purified by chromatography,recrystallization, and the like.

(Production Process 19)

The present compound (P7) represented by the formula (1) wherein R⁵ is aC1-C6 perfluoroalkyl group can be produced by reacting the presentcompound (P4) represented by the formula (1) wherein R⁵ is a halogenatom, the intermediate compound (M11) or the intermediate compound(M11′) in the presence of a copper compound.

wherein V¹ represents a halogen atom, Rf represents a C1-C6perfluoroalkyl group, and the other symbols are as defined in theformula (1).

The reaction is generally conducted in the presence of a solvent.

Examples of the solvent to be used in the reaction include aromatichydrocarbons such as toluene and xylene; aprotic polar solvents such asDMF, NMP, and DMSO; and mixtures thereof.

Examples of the copper compound to be used in the reaction includecopper, copper (I) iodide.

When the intermediate compound (M11) is used, the amount of theintermediate compound (M11) to be used in the reaction is generally 1 to10 moles relative to 1 mole of the present compound (P4). The amount ofthe copper compound to be used in the reaction is generally 0.5 to 10moles relative to 1 mole of the present compound (P4). The reactiontemperature of the reaction is generally within a range of 100° C. to200° C. The reaction time of the reaction is generally within a range of0.5 to 48 hours.

When the intermediate compound (M11′) is used, the reaction may beconducted in the presence of potassium fluoride. The amount of theintermediate compound (M11′) to be used in the reaction is generally 1to 10 moles relative to 1 mole of the present compound (P4). The amountof the copper compound to be used in the reaction is generally 0.1 to 10moles relative to 1 mole of the present compound (P4). The amount of thepotassium fluoride to be used in the reaction is generally 0.1 to 5moles relative to 0.1 mole of the present compound (P4). The reactiontemperature of the reaction is generally within a range of 0° C. to 150°C. The reaction time of the reaction is generally within a range of 0.5to 48 hours.

After the completion of the reaction, the present compound (P7) can beisolated by post-treatments, for example, extracting the reactionmixture with an organic solvent, and drying and concentrating theorganic layer. The isolated present compound (P7) can be furtherpurified by chromatography, recrystallization, and the like.

In the reaction, V¹ is preferably a bromine atom and an iodine atom.

(Production Process 20)

The present compound (P9) wherein R⁵ is —SH can be produced by reactingthe present compound (P4) with a sulfating agent. The intermediatecompound (P9′), which is a disulfide of the present compound (P9), canbe produced by oxidizing the present compound (P9).

wherein V¹ represents a halogen atom, and the other symbols are asdefined in the formula (1).

The present compound (P9) can be produced by reacting the presentcompound (P4) with a thioesterificating agent and a catalyst.

The reaction is generally conducted in the presence of a solvent.

Examples of the solvent to be used in the reaction include aromatichydrocarbons such as toluene and xylene; aprotic polar solvents such asDMF, NMP, and DMSO; and mixtures thereof.

Examples of the thioesterificating agent to be used in the reactioninclude sodium sulfide, sodium sulfide 9-hydrate, and thiourea.

Examples of the catalyst to be used in the reaction include copper (I)chloride, copper (I) bromide, and copper (I) iodide.

The reaction may be conducted in the presence of a ligand.

Examples of the ligand to be used in the reaction include acetylacetone,salen, phenanthroline; and the like.

The reaction may be conducted in the presence of a base.

Examples of the base to be used in the reaction include inorganic basessuch as potassium carbonate, cesium carbonate, and tripotassiumphosphate; and organic bases triethylamine.

The amount of the thioesterificating agent to be used in the reaction isgenerally 1 to 10 moles relative to 1 mole of the intermediate compound(P4).

The amount of the catalyst to be used in the reaction is generally 0.1to 5 moles relative to 1 mole of the intermediate compound (P4).

The amount of the ligand to be used in the reaction is generally 1 to 2moles relative to 1 mole of the intermediate compound (P4).

The reaction temperature of the reaction is generally within a range of50° C. to 200° C. The reaction time of the reaction is generally withina range of 0.5 to 24 hours.

After the completion of the reaction, the present compound (P9) can beisolated by post-treatments, for example, extracting the reactionmixture with an organic solvent, and drying and concentrating theorganic layer. The isolated present compound (P9) can be furtherpurified by chromatography, recrystallization, and the like.

In the reaction, V¹ is preferably a bromine atom and an iodine atom.

In the reaction, the reaction from the present compound (P9) tointermediate compound (P9′) is easily progressed, and thus theintermediate compound (P9′) may be produced during the synthesis of thepresent compound (P9).

The intermediate compound (P9′) can be produced by reacting the presentcompound (P9) with an oxidant.

The reaction is generally conducted in the presence of a solvent.

Examples of the solvent to be used in the reaction include water;alcohols such as methanol and ethanol; ethers such as THF, ethyleneglycol dimethyl ether, tert-butylmethyl ether, and 1,4-dioxane; aromatichydrocarbons such as toluene and xylene; nitriles such as acetonitrile;aprotic polar solvents such as DMF, NMP, and DMSO; carboxylic acids suchas acetic acid; and mixtures thereof.

Examples of the oxidant to be used in the reaction include oxygen,iodine, hydrogen peroxide solution, potassium ferricyanide, and thelike.

The amount of the oxidant to be used in the reaction is generally 0.5 to10 moles relative to 1 mole of the intermediate compound (P9).

The reaction temperature of the reaction is generally within a range of0° C. to 100° C. The reaction time of the reaction is generally within arange of 0.1 to 24 hours.

After the completion of the reaction, the intermediate compound (P9′)can be isolated by post-treatments, for example, extracting the reactionmixture with an organic solvent, and drying and concentrating theorganic layer. The isolated intermediate compound (P9′) can be furtherpurified by chromatography, recrystallization, and the like.

The present compound (P9) can be produced by thioesterifying the presentcompound (P4) to give the intermediate compound (P9-1), and thenhydrolyzing the resulting intermediate compound (P9-1).

wherein R¹⁰′ is any of the groups other than a hydrogen atom for R¹⁰ inthe formula (1), and the other symbols are as defined in the formula(1).

The intermediate compound (P9-1) can be produced by reacting the presentcompound (P4) with a thioesterifying agent, in the presence of a baseand a catalyst.

The reaction is generally conducted in the presence of a solvent.

Examples of the solvent to be used in the reaction include aromatichydrocarbons such as toluene and xylene; aprotic polar solvents such asDMF, NMP, and DMSO; and mixtures thereof.

Examples of the thioesterifying agent to be used in the reaction includethiobenzoic acid, and the like.

Examples of the catalyst to be used in the reaction include copper (I)chloride, copper (I) bromide, and copper (I) iodide.

The reaction may be conducted in the presence of a ligand.

Examples of the ligand to be used in the reaction include acetylacetone,salen, phenanthroline; and the like.

Examples of the base to be used in the reaction include inorganic basessuch as potassium carbonate, cesium carbonate, and tripotassiumphosphate; and organic bases such as triethylamine.

The amount of the thioesterifying agent is generally 1 to 10 molesrelative to 1 mole of the present compound (P4).

The amount of the catalyst is generally 0.1 to 5 moles relative to 1mole of the present compound (P4).

The amount of the ligand is generally 0.1 to 5 moles relative to 1 moleof the present compound (P4).

The amount of the base is generally 1 to 2 moles relative to 1 mole ofthe present compound (P4).

The reaction temperature of the reaction is generally within a range of50° C. to 200° C. The reaction time of the reaction is generally withina range of 0.5 to 24 hours.

After the completion of the reaction, the intermediate compound (P9-1)can be isolated by post-treatments, for example, extracting the reactionmixture with an organic solvent, and drying and concentrating theorganic layer. The isolated intermediate compound (P9-1) can be furtherpurified by chromatography, recrystallization, and the like.

In the reaction, V¹ is preferably a bromine atom and an iodine atom.

The present compound (P9) can be produced by hydrolyzing theintermediate compound (P9-1).

When the hydrolysis is conducted in the presence of an acid, an aqueoussolution of the acid is generally used as a solvent.

Examples of the acid to be used in the reaction include mineral acidssuch as hydrochloric acid, nitric acid, phosphoric acid, and sulfuricacid; and carboxylic acids such as acetic acid and trifluoroacetic acid.

The reaction temperature of the reaction is generally within a range of0° C. to 100° C. The reaction time of the reaction is generally within arange of 0.1 to 24 hours.

After the completion of the reaction, the present compound (P9) can beisolated by post-treatments, for example, extracting the reactionmixture with an organic solvent, and drying and concentrating theorganic layer. The isolated present compound (P9) can be furtherpurified by chromatography, recrystallization, and the like.

When the hydrolysis is conducted in the presence of a base, the reactionis generally conducted in the presence of a solvent.

Examples of the solvent to be used in the reaction include ethers suchas THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and1,4-dioxane; alcohols such as methanol and ethanol; water; and mixturesthereof.

Examples of the base to be used in the reaction include alkali metalhydroxides such as sodium hydroxide and potassium hydroxide.

The amount of the base to be used in the reaction is generally 1 to 10moles relative to 1 mole of the intermediate compound (P9-1).

The reaction temperature of the reaction is generally within a range of0° C. to 120° C. The reaction time of the reaction is generally within arange of 0.1 to 24 hours.

After the completion of the reaction, the present compound (P9) can beisolated by post-treatments, for example, acidifying the reactionsolution, extracting the reaction mixture with an organic solvent, anddrying and concentrating the organic layer. The isolated presentcompound (P9) can be further purified by chromatography,recrystallization, and the like.

In the reaction, the reaction from the present compound (P9) tointermediate compound (P9′) is easily progressed, and thus theintermediate compound (P9′) may be produced during the synthesis of thepresent compound (P9).

(Production Process 21)

The present compound (P10-m0) wherein R⁵ is —S(O)_(m)R¹⁰′ and m is 0 canbe produced by reacting the present compound (P9) or a disulfidethereof, the intermediate compound (P9′), and the compound (M13). Thepresent compound (P10) represented by the formula (1) wherein R⁵ is—S(O)_(m)R¹⁰′ and m is 1 or 2 can be produced by oxidizing the presentcompound (P10-m0) wherein m is 0.

wherein R¹⁰′ is any of the groups other than a hydrogen atom for R¹⁰ inthe formula (1), L is a leaving group such as a chlorine atom, a bromineatom, an iodine atom, a trifluoromethanesulfonyloxy group and amethanesulfonyloxy group, and the other symbols are as defined in theformula (1).

The reaction is generally conducted in the presence of a solvent.

Examples of the solvent to be used in the reaction include ethers suchas THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and1,4-dioxane; aromatic hydrocarbons such as toluene and xylene; nitrilessuch as acetonitrile; aprotic polar solvents such as DMF, NMP, and DMSO;and mixtures thereof.

Examples of the base to be used in the reaction include alkali metal oralkaline earth metal hydrides such as sodium hydride, potassium hydride,calcium hydride; inorganic bases such as sodium carbonate and potassiumcarbonate; and organic bases such as triethylamine.

When the intermediate compound (P9′), which is a disulfide, is used, thereaction is generally conducted in the presence of a reductant.

Examples of the reductant to be used in the reaction include sodiumhydroxymethanesulfinate (trade name: Rongalite).

The amount of the base to be used in the reaction is generally 1 to 10moles relative to 1 mole of the present compound (P9).

When the intermediate compound (P9′), which is a disulfide, is used, theamount of the intermediate compound (M13) to be used in the reaction isgenerally 2 to 10 moles relative to 1 mole of the present compound(P9′). The amount of the base to be used in the reaction is generally 2to 10 moles relative to 1 mole of the present compound (P9). The amountof the reductant to be used in the reaction is generally 1 to 5 molesrelative to 1 mole of the present compound (P9).

The reaction temperature of the reaction is generally within a range of0° C. to 100° C. The reaction time of the reaction is generally within arange of 0.1 to 24 hours.

After the completion of the reaction, the present compound (P10-m0)wherein m is 0 can be isolated by post-treatments, for example,extracting the reaction mixture with an organic solvent, and drying andconcentrating the organic layer. The isolated present compound (P10-m0)wherein m is 0 can be further purified by chromatography,recrystallization, and the like.

Among the present compounds (P10-m0) wherein m is 0, the compoundwherein R¹⁰′ is a C1-C6 perfluoroalkyl group can be produced by reactingthe intermediate compound (P9′), perfluoroalkyl iodide and a reductant.

The reaction is generally conducted in the presence of a solvent.

Examples of the solvent to be used in the reaction include ethers suchas THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and1,4-dioxane; aromatic hydrocarbons such as toluene and xylene; nitrilessuch as acetonitrile; aprotic polar solvents such as DMF, NMP, and DMSO;and mixtures thereof.

Examples of the reductant to be used in the reaction includetetrakis(dimethylamino)ethylene.

Examples of the perfluoroalkyl iodide to be used in the reaction includetrifluoromethane iodide, pentafluoroethane iodide,heptafluoro-2-iodopropane, and the like.

The amount of the perfluoroalkyl iodide to be used in the reaction isgenerally 2 to 10 moles relative to 1 mole of the intermediate compound(P9′).

The amount of the reductant to be used in the reaction is generally 1 to5 moles relative to 1 mole of the intermediate compound (P9′).

The reaction temperature of the reaction is generally within a range of−80° C. to 50° C. The reaction time of the reaction is generally withina range of 0.1 to 24 hours.

After the completion of the reaction, the present compound (P10-m0)wherein m is 0 can be isolated by post-treatments, for example,extracting the reaction mixture with an organic solvent, and drying andconcentrating the organic layer. The isolated present compound (P10-m0)wherein m is 0 can be further purified by chromatography,recrystallization, and the like.

The present compound (P10) wherein m is 1 or 2 can be produced byreacting, the present compound (P10-m0) wherein m is 0 with an oxidant.

The reaction is generally conducted in the presence of a solvent.

Examples of the solvent to be used in the reaction include aliphatichalogenated hydrocarbons such as dichloromethane and chloroform;alcohols such as methanol and ethanol; acetic acid; water; and mixturesthereof.

Examples of the oxidant to be used in the reaction includem-chloroperbenzoic acid and hydrogen peroxide solution.

The reaction may be conducted in the presence of a catalyst.

Examples of the catalyst to be used in the reaction include sodiumtungstate.

The amount of oxidant is generally 1 to 5 moles relative to 1 mole ofthe present compound (P10-m0) wherein m is 0.

The amount of catalyst is generally 0.01 to 0.5 moles relative to 1 moleof the present compound (P10-m0) wherein m is 0.

In the production of the compound wherein m is 1, the amount of theoxidant is generally 0.8 to 1.2 moles relative to 1 mole of the presentcompound (P10-m0) wherein m is 0. The amount of the catalyst to be usedin the reaction is generally 0.0.05 to 0.2 moles relative to 1 mole ofthe present compound (P10-m0) wherein m is 0.

In the production of the compound wherein m is 2, the amount of theoxidant is generally 1.8 to 5 moles relative to 1 mole of the presentcompound (P10-m0) wherein m is 0. The amount of the catalyst to be usedin the reaction is generally 0.05 to 0.2 moles relative to 1 mole of thepresent compound (P10-m0) wherein m is 0.

The reaction temperature of the reaction is generally within a range of−20° C. to 120° C. The reaction time of the reaction is generally withina range of 0.1 to 12 hours.

After the completion of the reaction, the present compound (P10) whereinm is 1 or 2 can be isolated by post-treatments, for example, extractingthe reaction mixture with an organic solvent, optionally washing themixture with an aqueous solution of a reductant (e.g., sodium sulfiteand sodium thiosulfate), followed by an aqueous solution of a base(e.g., sodium hydrogen carbonate), and drying and concentrating theorganic layer. The isolated present compound (P10) wherein m is 1 or 2can be further purified by chromatography, recrystallization, and thelike.

(Production Process 22)

The present compound (P11) represented by the formula (1) wherein R⁵ is—OH can be produced via the intermediate compound (P11′) from thepresent compound (P4).

wherein V¹ represents a halogen atom, and the other symbols are asdefined in the formula (1).

The intermediate compound (P11′) can be produced by reacting the presentcompound (P4) with benzyl alcohol in the presence of a base.

The reaction is generally conducted in the presence of a solvent or usedbenzyl alcohol as a solvent.

Examples of the solvent to be used in the reaction include aromatichydrocarbons such as toluene and xylene; aprotic polar solvents such asDMF, NMP, and DMSO; and mixtures thereof.

The reaction may be conducted in the presence of a catalyst.

Examples of the catalyst to be used in the reaction include copper (I)chloride, copper (I) bromide, and copper (I) iodide.

The reaction may be conducted in the presence of a ligand.

Examples of the ligand to be used in the reaction include acetylacetone,salen, phenanthroline; and the like.

The reaction is generally conducted in the presence of a base.

Examples of the base to be used in the reaction include inorganic basessuch as potassium carbonate, cesium carbonate, and tripotassiumphosphate.

The amount of the benzyl alcohol is generally 1 to 10 moles relative to1 mole of the present compound (P4).

The amount of the catalyst is generally 0.1 to 5 moles relative to 1mole of the present compound (P4).

The amount of the ligand is generally 0.1 to 5 moles relative to 1 moleof the present compound (P4).

The amount of the base is generally 1 to 2 moles relative to 1 mole ofthe present compound (P4).

The reaction temperature of the reaction is generally within a range of50° C. to 200° C. The reaction time of the reaction is generally withina range of 0.5 to 24 hours.

After the completion of the reaction, the intermediate compound (P11′)can be isolated by post-treatments, for example, extracting the reactionmixture with an organic solvent, and drying and concentrating theorganic layer. The isolated intermediate compound (P11′) can be furtherpurified by chromatography, recrystallization, and the like.

In the reaction, V¹ is preferably a bromine atom and an iodine atom.

The present compound (P11) can be produced by reacting the intermediatecompound (P11′) with hydrogen in the presence of a hydrogenatingcatalyst.

The reaction is generally conducted in the presence of a solvent underof hydrogen atmosphere at 1 to 100 atm.

Examples of the solvent to be used in the reaction include ethers suchas THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and1,4-dioxane; esters such as ethyl acetate and butyl acetate; alcoholssuch as methanol and ethanol; water; and mixtures thereof.

Examples of the hydrogenating catalyst to be used in the reactioninclude transition metal compounds such as palladium carbon, palladiumhydroxide, Raney nickel, and platinum oxide.

The amount of the hydrogen to be used in the reaction is generally 3moles relative to 1 mole of the intermediate compound (P11′).

The amount of the hydrogenating catalyst to be used in the reaction isgenerally 0.001 to 0.5 moles relative to 1 mole of the intermediatecompound (P11′).

The reaction may be conducted in the presence of an acid or a base.

Examples of the acid to be used in the reaction include acetic acid,hydrochloric acid, and the like.

Examples of the base to be used in the reaction include tertiary aminessuch as triethylamine; magnesium oxide; and the like.

The reaction temperature of the reaction is generally within a range of−20° C. to 100° C. The reaction time of the reaction is generally withina range of 0.1 to 24 hours.

After the completion of the reaction, the present compound (P11) can beisolated by post-treatments, for example, filtrating the reactionmixture, extracting the reaction mixture with an organic solvent, anddrying and concentrating the organic layer. The isolated presentcompound (P11) can be further purified by chromatography,recrystallization, and the like.

(Production Process 23)

The present compound (P12) represented by the formula (1) wherein R⁵ is—OR¹⁰′ can be produced by reacting the present compound (P11) with thecompound (M13).

wherein R¹⁰′ is any of the groups other than a hydrogen atom for R¹⁰ inthe formula (1), and the other symbols are as defined in the formula(1).

The reaction is generally conducted in the presence of a solvent.

Examples of the solvent to be used in the reaction include ethers suchas THF, ethylene glycol dimethyl ether, tert-butylmethyl ether, and1,4-dioxane; aromatic hydrocarbons such as toluene and xylene; nitrilessuch as acetonitrile; aprotic polar solvents such as DMF, NMP, and DMSO;and mixtures thereof.

Examples of the base to be used in the reaction include alkali metal oralkaline earth metal hydrides such as sodium hydride, potassium hydride,calcium hydride; inorganic bases such as sodium carbonate and potassiumcarbonate; and organic bases such as triethylamine.

The amount of the compound (M13) is generally 1 to 10 moles relative to1 mole of the present compound (P11).

The amount of the base is generally 1 to 10 moles relative to 1 mole ofthe present compound (P11).

The reaction temperature of the reaction is generally within a range of0° C. to 100° C. The reaction time of the reaction is generally within arange of 0.1 to 24 hours.

After the completion of the reaction, the present compound (P12) can beisolated by post-treatments, for example, extracting the reactionmixture with an organic solvent, and drying and concentrating theorganic layer. The isolated present compound (P12) can be furtherpurified by chromatography, recrystallization, and the like.

Among the present compounds (P12), the present compound (P12) whereinR¹⁰′ is a trifluoromethyl group can be produced by the followingProduction process.

wherein the symbols are as defined in the formula (1).

The intermediate compound (P11″) can be produced by reacting the presentcompound (P11), a base, carbon disulfide and a methylating agent.

The reaction is conducted in the presence of a solvent.

Examples of the solvent to be used in the reaction include aprotic polarsolvents such as DMF, NMP, and DMSO.

Examples of the base to be used in the reaction include alkali metalhydrides such as sodium hydride.

Examples of the methylating agent to be used in the reaction includemethyl iodide.

The amount of the base is generally 1 to 2 moles relative to 1 mole ofthe present compound (P11).

The amount of the carbon disulfide is generally 1 to 10 moles relativeto 1 mole of the present compound (P11).

The amount of the methylating agent is generally 1 to 10 moles relativeto 1 mole of the present compound (P11).

The reaction temperature of the reaction is generally within a range of0° C. to 100° C. The reaction time of the reaction is generally within arange of 0.5 to 24 hours.

After the completion of the reaction, the intermediate compound (P11″)can be isolated by post-treatments, for example, extracting the reactionmixture with an organic solvent, and drying and concentrating theorganic layer. The isolated intermediate compound (P11″) can be furtherpurified by chromatography, recrystallization, and the like.

Among the present compounds (P12), the present compound (P12) whereinR¹⁰′ is a trifluoromethyl group can be produced by reacting theintermediate compound (P11″) with a fluorinating agent in the presenceof a base.

The reaction is conducted in the presence of a solvent.

Examples of the solvent to be used in the reaction include halogenatedhydrocarbons such as dichloromethane, chloroform, carbon tetrachloride,and 1,2-dichloro ethane.

The reaction is conducted in the presence of a base and a fluorinatingagent.

Examples of the base to be used in the reaction include1,3-dibromo-5,5-dimethyl hydantoin.

Examples of the fluorinating agent to be used in the reaction includetetra-n-butylammonium fluoride, and hydrogen fluoride pyridine complex.

The amount of the base to be used in the reaction is generally 1 to 10moles relative to 1 mole of the intermediate compound (P11″).

The amount of the fluorinating agent is generally 1 to 10 moles relativeto 1 mole of the intermediate compound (P11″).

The reaction temperature of the reaction is generally within a range of−80° C. to 50° C. The reaction time of the reaction is generally withina range of 0.5 to 24 hours.

After the completion of the reaction, the present compound (P12) whereinR¹⁰′ is a trifluoromethyl group can be isolated by post-treatments, forexample, extracting the reaction mixture with an organic solvent, anddrying and concentrating the organic layer. The isolated presentcompound (P12) wherein R¹⁰′ is a trifluoromethyl group can be furtherpurified by chromatography, recrystallization, and the like.

(Production Process 25)

An N-oxide having an oxidized nitrogen atom of the present compound orthe intermediate compound can be produced by reacting a compound havinga nitrogen-containing heterocyclic group having a lone electron pair onthe nitrogen atom with an oxidant.

Examples of the nitrogen-containing heterocyclic group to be used in thereaction include a pyridine ring.

The reaction can be conducted by, for example, a known method in thepresence of a solvent such as halogenated hydrocarbons such asdichloromethane, chloroform, and chlorobenzene; alcohols such asmethanol and ethanol; acetic acid; water; and the mixtures thereof, byusing an oxidant such as m-chloroperbenzoic acid or hydrogen peroxide.

Examples of the intermediate compound (M3) include the followingcompounds.

A compound represented by the formula (M3) wherein A¹ is —NR⁷—;

A compound represented by the formula (M3) wherein A¹ is an oxygen atom;

A compound represented by the formula (M3) wherein A¹ is a sulfur atom;

A compound represented by the formula (M3) wherein A² is ═CR⁸—;

A compound represented by the formula (M3) wherein A² is ═CR⁸—, and A³is a nitrogen atom;

A compound represented by the formula (M3) wherein A² is ═CR⁸—, and A³is ═CR⁹—;

A compound represented by the formula (M3) wherein A¹ is —NR⁷—, and A²is ═CR⁸—;

A compound represented by the formula (M3) wherein A¹ is —NR⁷—, A² is═CR⁸—, and A³ is a nitrogen atom;

A compound represented by the formula (M3) wherein A¹ is —NR⁷—, A² is═CR⁸—, and A³ is ═CR⁹—;

A compound represented by the formula (M3) wherein A¹ is an oxygen atom,and A² is ═CR⁸—;

A compound represented by the formula (M3) wherein A¹ is an oxygen atom,A² is ═CR⁸—, and A³ is a nitrogen atom;

A compound represented by the formula (M3) wherein A¹ is an oxygen atom,A² is ═CR⁸—, and A³ is ═CR⁹—;

A compound represented by the formula (M3) wherein A¹ is a sulfur atom,and A² is ═CR⁸—;

A compound represented by the formula (M3) wherein A¹ is a sulfur atom,A² is —CR⁸—, and A³ is a nitrogen atom;

A compound represented by the formula (M3) wherein A¹ is a sulfur atom,A² is ═CR⁸—, and A³ is ═CR⁹—;

A compound represented by the formula (M3), which is represented by theformula (M3-1):

wherein the symbols are as defined in the formula (1-1);

A compound represented by the formula (M3-1) wherein A^(1a) is—NR^(7a)—;

A compound represented by the formula (M3-1) wherein A^(1a) is an oxygenatom;

A compound represented by the formula (M3-1) wherein A^(1a) is a sulfuratom;

A compound represented by the formula (M3-1) wherein A^(1a) is—NR^(7a)—, and A^(3a) is a nitrogen atom;

A compound represented by the formula (M3-1) wherein A^(1a) is—NR^(7a)—, and A^(3a) is ═CR^(9a)— compound;

A compound represented by the formula (M3-1) wherein A^(1a) is an oxygenatom, and A^(3a) is a nitrogen atom;

A compound represented by the formula (M3-1) wherein A^(1a) is an oxygenatom, and A^(3a) is ═CR^(9a)— compound;

A compound represented by the formula (M3-1) wherein A^(1a) is a sulfuratom, and A^(3a) is a nitrogen atom;

A compound represented by the formula (M3-1) wherein A^(1a) is a sulfuratom, and A^(3a) is ═CR^(9a)— compound;

A compound represented by the formula (M3-1), which is represented bythe formula (M3-2):

the formula (M3-2)

wherein the symbols are as defined in the formula (1-2);

A compound represented by the formula (M3-2) wherein A^(3b) is anitrogen atom;

A compound represented by the formula (M3-2) wherein A^(3b) is ═CR^(9b)—compound;

A compound represented by the formula (M3-1), which is represented bythe formula (M3-3):

wherein the symbols are as defined in the formula (1-2);

A compound represented by the formula (M3-3) wherein A^(3b) is anitrogen atom;

A compound represented by the formula (M3-3) wherein A^(3b) is ═CR^(9b)—compound;

A compound represented by the formula (M3-1), which is represented bythe formula (M3-4):

wherein the symbols are as defined in the formula (1-2);

A compound represented by the formula (M3-4) wherein A^(3b) is anitrogen atom;

A compound represented by the formula (M3-4) wherein A^(3b) is ═CR^(9b)—compound;

Examples of the intermediate compound (M6) include the followingcompounds.

A compound represented by the formula (M6) wherein A¹ is —NR⁷—;

A compound represented by the formula (M6) wherein A¹ is an oxygen atom;

A compound represented by the formula (M6) wherein A¹ is a sulfur atom;

A compound represented by the formula (M6) wherein A² is ═CR⁸—;

A compound represented by the formula (M6) wherein A² is ═CR⁸—, and A³is a nitrogen atom;

A compound represented by the formula (M6) wherein A² is ═CR⁸—, and A³is ═CR⁹—;

A compound represented by the formula (M6) wherein A¹ is —NR⁷—, and A²is ═CR⁸—;

A compound represented by the formula (M6) wherein A¹ is —NR⁷—, A² is═CR⁸—, and A³ is a nitrogen atom;

A compound represented by the formula (M6) wherein A¹ is —NR⁷—, A² is═CR⁸—, and A³ is ═CR⁹—;

A compound represented by the formula (M6) wherein A¹ is an oxygen atom,and A² is ═CR⁸—;

A compound represented by the formula (M6) wherein A¹ is an oxygen atom,A² is ═CR⁸—, and A³ is a nitrogen atom;

A compound represented by the formula (M6) wherein A¹ is an oxygen atom,A² is ═CR⁸—, and A³ is ═CR⁹—;

A compound represented by the formula (M6) wherein A¹ is a sulfur atom,and A² is ═CR⁸—;

A compound represented by the formula (M6) wherein A¹ is a sulfur atom,A² is ═CR⁸—, and A³ is a nitrogen atom;

A compound represented by the formula (M6) wherein A¹ is a sulfur atom,A² is ═CR⁸—, and A³ is ═CR⁹—;

A compound represented by the formula (M6), which is represented by theformula (M6-1):

wherein V² represents a halogen atom, and the other symbols are asdefined in the formula (1-1);

A compound represented by the formula (M6-1) wherein A^(1a) is—NR^(7a)—;

A compound represented by the formula (M6-1) wherein A^(1a) is an oxygenatom;

A compound represented by the formula (M6-1) wherein A^(1a) is a sulfuratom;

A compound represented by the formula (M6-1) wherein A^(1a) is—NR^(7a)—, and A^(3a) is a nitrogen atom;

A compound represented by the formula (M6-1) wherein A^(1a) is—NR^(7a)—, and A^(3a) is ═CR^(9a)— compound;

A compound represented by the formula (M6-1) wherein A^(1a) is an oxygenatom, and A^(3a) is a nitrogen atom;

A compound represented by the formula (M6-1) wherein A^(1a) is an oxygenatom, and A^(3a) is ═CR^(9a)— compound;

A compound represented by the formula (M6-1) wherein A^(1a) is a sulfuratom, and A^(3a) is a nitrogen atom;

A compound represented by the formula (M6-1) wherein A^(1a) is a sulfuratom, and A^(3a) is ═CR^(9a)— compound;

A compound represented by the formula (M6-1), which is represented bythe formula (M6-2):

wherein V² represents a halogen atom, and the other symbols are asdefined in the formula (1-2);

A compound represented by the formula (M6-2) wherein A^(3b) is anitrogen atom;

A compound represented by the formula (M6-2) wherein A^(3b) is ═CR^(9b)—compound;

A compound represented by the formula (M6-1), which is represented bythe formula (M6-3):

wherein V² represents a halogen atom, and the other symbols are asdefined in the formula (1-2);

A compound represented by the formula (M6-3) wherein A^(3b) is anitrogen atom;

A compound represented by the formula (M6-3) wherein A^(3b) is ═CR^(9b)—compound;

A compound represented by the formula (M6-1), which is represented bythe formula (M6-4):

wherein V² represents a halogen atom, and the other symbols are asdefined in the formula (1-2);

A compound represented by the formula (M6-4) wherein A^(3b) is anitrogen atom;

A compound represented by the formula (M6-4) wherein A^(3b) is ═CR^(9b)—compound;

Examples of the intermediate compound (M8) and a disulfide thereof (M8′)include the following compounds.

A compound represented by the formula (M8) or (M8′) wherein A¹ is —NR⁷—;

A compound represented by the formula (M8) or (M8′) wherein A¹ is anoxygen atom;

A compound represented by the formula (M8) or (M8′) wherein A¹ is asulfur atom;

A compound represented by the formula (M8) or (M8′) wherein A² is ═CR⁸—;

A compound represented by the formula (M8) or (M8′) wherein A² is ═CR⁸—,and A³ is a nitrogen atom;

A compound represented by the formula (M8) or (M8′) wherein A² is ═CR⁸—,and A³ is ═CR⁹—;

A compound represented by the formula (M8) or (M8′) wherein A¹ is —NR⁷—,and A² is ═CR⁸—;

A compound represented by the formula (M8) or (M8′) wherein A¹ is —NR⁷—,A² is ═CR⁸—, and A³ is a nitrogen atom;

A compound represented by the formula (M8) or (M8′) wherein A¹ is —NR⁷—,A² is ═CR⁸—, and A³ is ═CR⁹—;

A compound represented by the formula (M8) or (M8′) wherein A¹ is anoxygen atom, and A² is ═CR⁸—;

A compound represented by the formula (M8) or (M8′) wherein A¹ is anoxygen atom, A² is ═CR⁸—, and A³ is a nitrogen atom;

A compound represented by the formula (M8) or (M8′) wherein A¹ is anoxygen atom, A² is ═CR⁸—, and A³ is ═CR⁹—;

A compound represented by the formula (M8) or (M8′) wherein A¹ is asulfur atom, and A² is ═CR⁸—;

A compound represented by the formula (M8) or (M8′) wherein A¹ is asulfur atom, A² is CR⁸—, and A is a nitrogen atom;

A compound represented by the formula (M8) or (M8′) wherein A¹ is asulfur atom, A² is ═CR⁸—, and A³ is ═CR⁹—;

A compound represented by the formula (M8), which is represented by theformula (M8-1):

wherein the symbols are as defined in the formula (1-1), or a compoundrepresented by the formula (M8′), which is a disulfide thereof andrepresented by the formula (M8′-1):

wherein the symbols are as defined in the formula (1-1);

A compound represented by the formula (M8-1) or (M8′-1) wherein A^(1a)is —NR^(7a)—;

A compound represented by the formula (M8-1) or (M8′-1) wherein A^(1a)is an oxygen atom;

A compound represented by the formula (M8-1) or (M8′-1) wherein A^(1a)is a sulfur atom;

A compound represented by the formula (M8-1) or (M8′-1) wherein A^(1a)is —NR^(7a)—, and A^(3a) is a nitrogen atom;

A compound represented by the formula (M8-1) or (M8′-1) wherein A^(1a)is —NR^(7a)—, and A^(3a) is ═CR^(9a)— compound;

A compound represented by the formula (M8-1) or (M8′-1) wherein A^(1a)is an oxygen atom, and A^(3a) is a nitrogen atom;

A compound represented by the formula (M8-1) or (M8′-1) wherein A^(1a)is an oxygen atom, and A^(3a) is ═CR^(9a)— compound;

A compound represented by the formula (M8-1) or (M8′-1) wherein A^(1a)is a sulfur atom, and A^(3a) is a nitrogen atom;

A compound represented by the formula (M8-1) or (M8′-1) wherein A^(1a)is a sulfur atom, and A^(3a) is ═CR^(9a)— compound;

A compound represented by the formula (M8-1), which is represented bythe formula (M8-2):

wherein the symbols are as defined in the formula (1-2) or a compoundrepresented by the formula (M8′-1), which is a disulfide thereof andrepresented by the formula (M8′-2):

wherein the symbols are as defined in the formula (1-2);

A compound represented by the formula (M8-2) or (M8′-2) wherein A^(3b)is a nitrogen atom;

A compound represented by the formula (M8-2) or (M8′-2) wherein A^(3b)is ═CR^(9b)— compound;

A compound represented by the formula (M8-1), which is represented bythe formula (M8-3):

wherein the symbols are as defined in the formula (1-2) or a compoundrepresented by the formula (M8′-1), which is a disulfide thereof andrepresented by the formula (M8′-3):

wherein the symbols are as defined in the formula (1-2).

A compound represented by the formula (M8-3) or (M8′-3) wherein A^(3b)is a nitrogen atom;

A compound represented by the formula (M8-3) or (M8′-3) wherein A^(3b)is ═CR^(9b)— compound;

A compound represented by the formula (M8-1), which is represented bythe formula (M8-4):

wherein the symbols are as defined in the formula (1-2) or a compoundrepresented by the formula (M8′-1), which is a disulfide thereof andrepresented by the formula (M8′-4):

wherein the symbols are as defined in the formula (1-2).

A compound represented by the formula (M8-4) or (M8′-4) wherein A^(3b)is a nitrogen atom;

A compound represented by the formula (M8-4) or (M8′-4) wherein A^(3b)is ═CR^(9b)— compound;

Examples of the intermediate compound (M20) include the followingcompounds.

A compound represented by the formula (M20) wherein A¹ is —NR⁷—;

A compound represented by the formula (M20) wherein A¹ is an oxygenatom;

A compound represented by the formula (M20) wherein A¹ is a sulfur atom;

A compound represented by the formula (M20) wherein A² is ═CR⁸—;

A compound represented by the formula (M20) wherein A² is ═CR⁸—, and A³is a nitrogen atom;

A compound represented by the formula (M20) wherein A² is ═CR⁸—, and A³is ═CR⁹—;

A compound represented by the formula (M20) wherein A¹ is —NR⁷—, and A²is ═CR⁸—;

A compound represented by the formula (M20) wherein A¹ is —NR⁷—, A² is═CR⁸—, and A³ is a nitrogen atom;

A compound represented by the formula (M20) wherein A¹ is —NR⁷—, A² is═CR⁸—, and A³ is ═CR⁹—;

A compound represented by the formula (M20) wherein A is an oxygen atom,and A² is ═CR⁸—;

A compound represented by the formula (M20) wherein A¹ is an oxygenatom, A² is ═CR⁸—, and A³ is a nitrogen atom;

A compound represented by the formula (M20) wherein A¹ is an oxygenatom, A² is ═CR⁸—, and A³ is ═CR⁹—;

A compound represented by the formula (M20) wherein A¹ is a sulfur atom,and A² is ═CR⁸—;

A compound represented by the formula (M20) wherein A¹ is a sulfur atom,A² is ═CR⁸—, and A³ is a nitrogen atom;

A compound represented by the formula (M20) wherein A¹ is a sulfur atom,A² is ═CR⁸—, and A³ is ═CR⁹—;

A compound represented by the formula (M20) wherein R² and R⁴ is ahydrogen atom;

A compound represented by the formula (M20), which is represented by theformula (M20-1):

wherein V² represents a halogen atom, and the other symbols are asdefined in the formula (1-1);

A compound represented by the formula (M20-1) wherein A^(1a) is—NR^(7a)—;

A compound represented by the formula (M20-1) wherein A^(1a) is anoxygen atom;

A compound represented by the formula (M20-1) wherein A^(1a) is a sulfuratom;

A compound represented by the formula (M20-1) wherein A^(1a) is—NR^(7a)—, and A^(3a) is a nitrogen atom;

A compound represented by the formula (M20-1) wherein A^(1a) is—NR^(9a)—, and A^(3a) is ═CR^(9a)— compound;

A compound represented by the formula (M20-1) wherein A^(1a) is anoxygen atom, and A^(3a) is a nitrogen atom;

A compound represented by the formula (M20-1) wherein A^(1a) is anoxygen atom, and A^(3a) is ═CR^(9a)— compound;

A compound represented by the formula (M20-1) wherein A^(1a) is a sulfuratom, and A^(3a) is a nitrogen atom;

A compound represented by the formula (M20-1) wherein A^(1a) is a sulfuratom, and A^(3a) is ═CR^(9a)— compound;

A compound represented by the formula (M20-1) wherein R^(2a) and R^(4a)is a hydrogen atom;

A compound represented by the formula (M20-1), which is represented bythe formula (M20-2):

wherein V² represents a halogen atom, and the other symbols are asdefined in the formula (1-2);

A compound represented by the formula (M20-2) wherein A^(3b) is anitrogen atom;

A compound represented by the formula (M20-2) wherein A^(3b) is═CR^(9b)— compound;

A compound represented by the formula (M20-1), which is represented bythe formula (M20-3):

wherein V² represents a halogen atom, and the other symbols are asdefined in the formula (1-2);

A compound represented by the formula (M20-3) wherein A^(3b) is anitrogen atom;

A compound represented by the formula (M20-3) wherein A^(3b) is═CR^(9b)— compound;

A compound represented by the formula (M20-1), which is represented bythe formula (M20-4):

wherein V² represents a halogen atom, and the other symbols are asdefined in the formula (1-2);

A compound represented by the formula (M20-4) wherein A^(3b) is anitrogen atom;

A compound represented by the formula (M20-4) wherein A^(3b) is═CR^(9b)— compound;

As described above, the compound represented by the formula (P4) amongthe present compounds can be used as an intermediate in the productionof the present compound.

Examples of the present compound (P4) represented by the formula (1)include the following compounds.

A compound represented by the formula (P4) wherein A³ is —NR⁷—;

A compound represented by the formula (P4) wherein A¹ is an oxygen atom;

A compound represented by the formula (P4) wherein A¹ is a sulfur atom;

A compound represented by the formula (P4) wherein A² is ═CR⁸—;

A compound represented by the formula (P4) wherein A² is ═CR⁸—, and A³is a nitrogen atom;

A compound represented by the formula (P4) wherein A² is ═CR⁸—, and A is═CR⁹—;

A compound represented by the formula (P4) wherein A¹ is —NR⁷—, and A²is ═CR⁸—;

A compound represented by the formula (P4) wherein A¹ is —NR⁷—, A² is═CR⁸—, and A³ is a nitrogen atom;

A compound represented by the formula (P4) wherein A¹ is —NR⁷—, A² is═CR⁸—, and A³ is ═CR⁹—;

a compound represented by the formula (P4) wherein A¹ is an oxygen atom,and A² is ═CR⁸—;

A compound represented by the formula (P4) wherein A¹ is an oxygen atom,A² is ═CR⁸—, and A³ is a nitrogen atom;

A compound represented by the formula (P4) wherein A¹ is an oxygen atom,A² is ═CR⁸—, and A³ is ═CR⁹—;

A compound represented by the formula (P4) wherein A¹ is a sulfur atom,and A² is ═CR⁹—;

A compound represented by the formula (P4) wherein A¹ is a sulfur atom,A² is ═CR⁸—, and A³ is a nitrogen atom;

A compound represented by the formula (P4) wherein A¹ is a sulfur atom,A² is ═CR⁸—, and A³ is ═CR⁹—;

A compound represented by the formula (P4), which is represented by theformula (P4-1):

wherein V¹ represents a halogen atom, and the other symbols are asdefined in the formula (1-1);

A compound represented by the formula (P4-1) wherein A^(1a) is—NR^(7a)—;

A compound represented by the formula (P4-1) wherein A^(1a) is an oxygenatom;

A compound represented by the formula (P4-1) wherein A^(1a) is a sulfuratom;

A compound represented by the formula (P4-1) wherein A^(1a) is—NR^(7a)—, and A^(3a) is a nitrogen atom;

A compound represented by the formula (P4-1) wherein A^(1a) is—NR^(7a)—, and A^(3a) is ═CR^(9a)— compound;

A compound represented by the formula (P4-1) wherein A^(1a) is an oxygenatom, and A^(3a) is a nitrogen atom;

A compound represented by the formula (P4-1) wherein A^(1a) is an oxygenatom, and A^(3a) is ═CR^(9a)— compound;

A compound represented by the formula (P4-1) wherein A^(1a) is a sulfuratom, and A^(3a) is a nitrogen atom;

A compound represented by the formula (P4-1) wherein A^(1a) is a sulfuratom, and A^(3a) is ═CR^(9a)— compound;

A compound represented by the formula (P4-1), which is represented bythe formula (P4-2):

wherein V¹ represents a halogen atom, and the other symbols are asdefined in the formula (1-2);

A compound represented by the formula (P4-2) wherein A^(3b) is anitrogen atom;

A compound represented by the formula (P4-2) wherein A^(3b) is ═CR^(9b)—compound;

A compound represented by the formula (P4-1), which is represented bythe formula (P4-3):

wherein V¹ represents a halogen atom, and the other symbols are asdefined in the formula (1-2);

A compound represented by the formula (P4-3) wherein A^(3b) is anitrogen atom;

A compound represented by the formula (P4-3) wherein A^(3b) is ═CR^(9b)—compound;

A compound represented by the formula (P4-1), which is represented bythe formula (P4-4):

wherein V¹ represents a halogen atom, and the other symbols are asdefined in the formula (1-2);

A compound represented by the formula (P4-4) wherein A^(3b) is anitrogen atom;

A compound represented by the formula (P4-4) wherein A^(3b) is ═CR^(9b)—compound.

As described above, the compound represented by the formula (P9) amongthe present compounds can be used as an intermediate in the productionof the present compound.

The present compound (P9) represented by the formula (1) and a disulfidethereof (P9′) include the following compounds.

A compound represented by the formula (P9) or the formula (P9′) whereinA¹ is —NR⁷—;

A compound represented by the formula (P9) or the formula (P9′) whereinA¹ is an oxygen atom;

A compound represented by the formula (P9) or the formula (P9′) whereinA¹ is a sulfur atom;

A compound represented by the formula (P9) or the formula (P9′) whereinA² is ═CR⁸—;

A compound represented by the formula (P9) or the formula (P9′) whereinA² is ═CR⁸—, and A³ is a nitrogen atom;

A compound represented by the formula (P9) or the formula (P9′) whereinA² is ═CR⁸—, and A³ is ═CR⁹—;

A compound represented by the formula (P9) or the formula (P9′) whereinA¹ is —NR⁷—, and A² is ═CR⁸—;

A compound represented by the formula (P9) or the formula (P9′) whereinA¹ is —NR⁷—, A² is ═CR⁸—, and A³ is a nitrogen atom;

A compound represented by the formula (P9) or the formula (P9′) whereinA¹ is —NR⁷—, A² is ═CR⁸—, and A³ is ═CR⁹—;

A compound represented by the formula (P9) or the formula (P9′) whereinA¹ is an oxygen atom, and A² is ═CR⁸—;

A compound represented by the formula (P9) or the formula (P9′) whereinA¹ is an oxygen atom, A² is ═CR⁸—, and A³ is a nitrogen atom;

A compound represented by the formula (P9) or the formula (P9′) whereinA¹ is an oxygen atom, A² is ═CR⁸—, and A³ is ═CR⁹—;

A compound represented by the formula (P9) or the formula (P9′) whereinA¹ is a sulfur atom, and A² is ═CR⁸—;

A compound represented by the formula (P9) or the formula (P9′) whereinA¹ is a sulfur atom, A² is ═CR⁸—, and A³ is a nitrogen atom;

A compound represented by the formula (P9) or the formula (P9′) whereinA¹ is a sulfur atom, A² is ═CR⁸—, and A³ is ═CR⁹—;

A compound represented by the formula (P9), which is represented by theformula (P9-1):

wherein the symbols are as defined in the formula (1-1), or a compoundrepresented by the formula (M9′), which is a disulfide thereof andrepresented by the formula (M9′-1):

wherein the symbols are as defined in the formula (1-1);

A compound represented by the formula (P9-1) or (P9′-1) wherein A^(1a)is —NR^(7a)—;

A compound represented by the formula (P9-1) or (P9′-1) wherein A^(1a)is an oxygen atom;

A compound represented by the formula (P9-1) or (P9′-1) wherein A^(1a)is a sulfur atom;

A compound represented by the formula (P9-1) or (P9′-1) wherein A^(1a)is —NR^(7a)—, and A^(3a) is a nitrogen atom;

A compound represented by the formula (P9-1) or (P9′-1) wherein A^(1a)is —NR^(7a)—, and A^(3a) is ═CR^(9a)— compound;

A compound represented by the formula (P9-1) or (P9′-1) wherein A^(1a)is an oxygen atom, and A^(3a) is a nitrogen atom;

A compound represented by the formula (P9-1) or (P9′-1) wherein A^(1a)is an oxygen atom, and A^(3a) is ═CR^(9a)— compound;

A compound represented by the formula (P9-1) or (P9′-1) wherein A^(1a)is a sulfur atom, and A^(3a) is a nitrogen atom;

A compound represented by the formula (P9-1) or (P9′-1) wherein A^(1a)is a sulfur atom, and A^(3a) is ═CR^(9a)— compound;

A compound represented by the formula (P9-1), which is represented bythe formula (P9-2):

wherein the symbols are as defined in the formula (1-2), or a compoundrepresented by the formula (M9′-1), which is a disulfide thereof andrepresented by the formula (M9′-2):

wherein, the symbols are as defined in the formula (1-2);

A compound represented by the formula (P9-2) or (P9′-2) wherein A^(3b)is a nitrogen atom;

A compound represented by the formula (P9-2) or (P9′-2) wherein A^(3b)is ═CR^(9b)— compound;

A compound represented by the formula (P9-1), which is represented bythe formula (P9-3):

wherein the symbols are as defined in the formula (1-2), or a compoundrepresented by the formula (M9′-1), which is a disulfide thereof andrepresented by the formula (M9′-3):

wherein the symbols are as defined in the formula (1-2);

A compound represented by the formula (P9-3) or (P9′-3) wherein A^(3b)is a nitrogen atom;

A compound represented by the formula (P9-3) or (P9′-3) wherein A^(3b)is ═CR^(9b)— compound;

A compound represented by the formula (P9-1), which is represented bythe formula (P9-4):

wherein the symbols are as defined in the formula (1-2), or a compoundrepresented by the formula (M9′-1), which is a disulfide thereof andrepresented by the formula (M9′-4):

wherein the symbols are as defined in the formula (1-2);

A compound represented by the formula (P9-4) or (P9′-4) wherein A^(3b)is a nitrogen atom;

A compound represented by the formula (P9-4) or (P9′-4) wherein A^(3b)is ═CR^(9b)— compound;

As described above, the compound represented by the formula (P2) amongthe present compounds can be used as an intermediate in the productionof the present compound.

The present compound (P2) represented by the formula (1) include thefollowing compounds.

A compound represented by the formula (P2) wherein A² is ═CR⁸—;

A compound represented by the formula (P2) wherein A² is ═CR⁸—, and A³is a nitrogen atom;

A compound represented by the formula (P2) wherein A² is ═CR⁸—, and A³is ═CR⁹—;

A compound represented by the formula (P2), which is represented by theformula (P2-1):

wherein the symbols are as defined in the formula (1-1);

A compound represented by the formula (P2-1) wherein A^(3a) is anitrogen atom;

A compound represented by the formula (P2-1) wherein A^(3a) is ═CR^(9a)—compound;

A compound represented by the formula (P2-1), which is represented bythe formula (P2-2):

wherein the symbols are as defined in the formula (1-2);

A compound represented by the formula (P2-2) wherein A^(3a) is anitrogen atom;

A compound represented by the formula (P2-2) wherein A^(3a) is ═CR^(9a)—compound;

Examples of the intermediate compound (M2) include the followingcompounds.

A compound represented by the formula (M2), which is represented by theformula (M2-1):

wherein the symbols are as defined in the formula (1-1);

A compound represented by the formula (M2-1) wherein R^(1a) is an ethylgroup or a cyclopropylmethyl group, n is 1 or 2;

A compound represented by the formula (M2-1) wherein R^(1a) is an ethylgroup or a cyclopropylmethyl group, R^(3a) is a trifluoromethyl group;

A compound represented by the formula (M2-1), which is represented bythe formula (M2-2):

wherein the symbols are as defined in the formula (1-2);

A compound represented by the formula (M2-2) wherein R^(1b) is an ethylgroup or a cyclopropylmethyl group, n is 1 or 2;

A compound represented by the formula (M2-2) wherein R^(1b) is an ethylgroup or a cyclopropylmethyl group, R^(3b) is a trifluoromethyl group;

Examples of the intermediate compound (M18) include the followingcompounds.

A compound represented by the formula (M18), which is represented by theformula (M18-1):

wherein the symbols are as defined in the formula (1-1);

A compound represented by the formula (M18-1) wherein R^(1a) is an ethylgroup or a cyclopropylmethyl group;

A compound represented by the formula (M18-1), which is represented bythe formula (M18-2):

wherein the symbols are as defined in the formula (1-2);

A compound represented by the formula (M18-2) wherein R^(1b) is an ethylgroup or a cyclopropylmethyl group, R^(3b) is a hydrogen atom;

A compound represented by the formula (M18-2) wherein R^(1b) is an ethylgroup or a cyclopropylmethyl group, R^(3b) is a trifluoromethyl group;

Examples of the intermediate compound (M4) include the followingcompounds.

A compound represented by the formula (M4), which is represented by theformula (M4-1):

wherein the symbols are as defined in the formula (1-1);

A compound represented by the formula (M4-1) wherein R^(1a) is an ethylgroup or a cyclopropylmethyl group, R^(3a) is a hydrogen atom;

A compound represented by the formula (M4-1) wherein R^(1a) is an ethylgroup or a cyclopropylmethyl group, R^(3a) is a trifluoromethyl group;

A compound represented by the formula (M4-1), which is represented bythe formula (M4-2):

wherein the symbols are as defined in the formula (1-2);

A compound represented by the formula (M4-2) wherein R^(1b) is an ethylgroup or a cyclopropylmethyl group, R^(3b) is a hydrogen atom;

A compound represented by the formula (M4-2) wherein R^(1b) is an ethylgroup or a cyclopropylmethyl group, R^(3b) is a trifluoromethyl group;

Examples of the intermediate compound (M37) include the followingcompounds.

A compound represented by the formula (M37), which is represented by theformula (M37-1):

wherein the symbols are as defined in the formula (1-1);

A compound represented by the formula (M37-1) wherein R^(1a) is an ethylgroup or a cyclopropylmethyl group, n is 1 or 2;

A compound represented by the formula (M37-1) wherein R^(1a) is an ethylgroup or a cyclopropylmethyl group, R^(3a) is a trifluoromethyl group;

A compound represented by the formula (M37-1), which is represented bythe formula (M37-2):

wherein the symbols are as defined in the formula (1-2);

A compound represented by the formula (M37-2) wherein R^(1b) is an ethylgroup or a cyclopropylmethyl group, n is 1 or 2;

A compound represented by the formula (M37-2) wherein R^(1b) is an ethylgroup or a cyclopropylmethyl group, R^(3b) is a trifluoromethyl group.

Next, specific examples of the present compound are described below.

The present compound is represented by the formula (A):

wherein R², R³ and R⁴ are independently a hydrogen atom, R⁵ is atrifluoromethyl group, R¹, A¹, A³ and n represent any one of thecombinations as listed in [Table 1] to [Table 35].

TABLE 1 R¹ A¹ A³ n Me NMe N 0 Me NMe N 1 Me NMe N 2 Et NMe N 0 Et NMe N1 Et NMe N 2 Pr NMe N 0 Pr NMe N 1 Pr NMe N 2 iPr NMe N 0 iPr NMe N 1iPr NMe N 2 tBu NMe N 0 tBu NMe N 1 tBu NMe N 2 CF₃ NMe N 0 CF₃ NMe N 1CF₃ NMe N 2 CH₂CF₃ NMe N 0 CH₂CF₃ NMe N 1 CH₂CF₃ NMe N 2 CH═CH₂ NMe N 0CH═CH₂ NMe N 1 CH═CH₂ NMe N 2

TABLE 2 R¹ A¹ A³ n CH₂CH═CH₂ NMe N 0 CH₂CH═CH₂ NMe N 1 CH₂CH═CH₂ NMe N 2C≡CH NMe N 0 C≡CH NMe N 1 C≡CH NMe N 2 CH₂C≡CH NMe N 0 CH₂C≡CH NMe N 1CH₂C≡CH NMe N 2 CycPr NMe N 0 CycPr NMe N 1 CycPr NMe N 2 CH₂CycPr NMe N0 CH₂CycPr NMe N 1 CH₂CycPr NMe N 2 Me NMe CH 0 Me NMe CH 1 Me NMe CH 2Et NMe CH 0 Et NMe CH 1 Et NMe CH 2 Pr NMe CH 0 Pr NMe CH 1 Pr NMe CH 2

TABLE 3 R¹ A¹ A³ n iPr NMe CH 0 iPr NMe CH 1 iPr NMe CH 2 tBu NMe CH 0tBu NMe CH 1 tBu NMe CH 2 CF₃ NMe CH 0 CF₃ NMe CH 1 CF₃ NMe CH 2 CH₂CF₃NMe CH 0 CH₂CF₃ NMe CH 1 CH₂CF₃ NMe CH 2 CH═CH₂ NMe CH 0 CH═CH₂ NMe CH 1CH═CH₂ NMe CH 2 CH₂CH═CH₂ NMe CH 0 CH₂CH═CH₂ NMe CH 1 CH₂CH═CH₂ NMe CH 2C≡CH NMe CH 0 C≡CH NMe CH 1 C≡CH NMe CH 2 CH₂C≡CH NMe CH 0 CH₂C≡CH NMeCH 1 CH₂C≡CH NMe CH 2

TABLE 4 R¹ A¹ A³ n CycPr NMe CH 0 CycPr NMe CH 1 CycPr NMe CH 2 CH₂CycPrNMe CH 0 CH₂CycPr NMe CH 1 CH₂CycPr NMe CH 2 Me NMe CBr 0 Me NMe CBr 1Me NMe CBr 2 Et NMe CBr 0 Et NMe CBr 1 Et NMe CBr 2 Pr NMe CBr 0 Pr NMeCBr 1 Pr NMe CBr 2 iPr NMe CBr 0 iPr NMe CBr 1 iPr NMe CBr 2 tBu NMe CBr0 tBu NMe CBr 1 tBu NMe CBr 2 CF₃ NMe CBr 0 CF₃ NMe CBr 1 CF₃ NMe CBr 2

TABLE 5 R¹ A¹ A³ n CH₂CF₃ NMe CBr 0 CH₂CF₃ NMe CBr 1 CH₂CF₃ NMe CBr 2CH═CH₂ NMe CBr 0 CH═CH₂ NMe CBr 1 CH═CH₂ NMe CBr 2 CH₂CH═CH₂ NMe CBr 0CH₂CH═CH₂ NMe CBr 1 CH₂CH═CH₂ NMe CBr 2 C≡CH NMe CBr 0 C≡CH NMe CBr 1C≡CH NMe CBr 2 CH₂C≡CH NMe CBr 0 CH₂C≡CH NMe CBr 1 CH₂C≡CH NMe CBr 2CycPr NMe CBr 0 CycPr NMe CBr 1 CycPr NMe CBr 2 CH₂CycPr NMe CBr 0CH₂CycPr NMe CBr 1 CH₂CycPr NMe CBr 2

TABLE 6 R¹ A¹ A³ n Me NH N 0 Me NH N 1 Me NH N 2 Et NH N 0 Et NH N 1 EtNH N 2 Pr NH N 0 Pr NH N 1 Pr NH N 2 iPr NH N 0 iPr NH N 1 iPr NH N 2tBu NH N 0 tBu NH N 1 tBu NH N 2 CF₃ NH N 0 CF₃ NH N 1 CF₃ NH N 2 CH₂CF₃NH N 0 CH₂CF₃ NH N 1 CH₂CF₃ NH N 2 CH═CH₂ NH N 0 CH═CH₂ NH N 1 CH═CH₂ NHN 2

TABLE 7 R¹ A¹ A³ n CH₂CH═CH₂ NH N 0 CH₂CH═CH₂ NH N 1 CH₂CH═CH₂ NH N 2C≡CH NH N 0 C≡CH NH N 1 C≡CH NH N 2 CH₂C≡CH NH N 0 CH₂C≡CH NH N 1CH₂C≡CH NH N 2 CycPr NH N 0 CycPr NH N 1 CycPr NH N 2 CH₂CycPr NH N 0CH₂CycPr NH N 1 CH₂CycPr NH N 2 Me NH CH 0 Me NH CH 1 Me NH CH 2 Et NHCH 0 Et NH CH 1 Et NH CH 2 Pr NH CH 0 Pr NH CH 1 Pr NH CH 2

TABLE 8 R¹ A¹ A³ n iPr NH CH 0 iPr NH CH 1 iPr NH CH 2 tBu NH CH 0 tBuNH CH 1 tBu NH CH 2 CF₃ NH CH 0 CF₃ NH CH 1 CF₃ NH CH 2 CH₂CF₃ NH CH 0CH₂CF₃ NH CH 1 CH₂CF₃ NH CH 2 CH═CH₂ NH CH 0 CH═CH₂ NH CH 1 CH═CH₂ NH CH2 CH₂CH═CH₂ NH CH 0 CH₂CH═CH₂ NH CH 1 CH₂CH═CH₂ NH CH 2 C≡CH NH CH 0C≡CH NH CH 1 C≡CH NH CH 2 CH₂C≡CH NH CH 0 CH₂C≡CH NH CH 1 CH₂C≡CH NH CH2

TABLE 9 R¹ A¹ A³ n CycPr NH CH 0 CycPr NH CH 1 CycPr NH CH 2 CH₂CycPr NHCH 0 CH₂CycPr NH CH 1 CH₂CycPr NH CH 2 Me NH CBr 0 Me NH CBr 1 Me NH CBr2 Et NH CBr 0 Et NH CBr 1 Et NH CBr 2 Pr NH CBr 0 Pr NH CBr 1 Pr NH CBr2 iPr NH CBr 0 iPr NH CBr 1 iPr NH CBr 2 tBu NH CBr 0 tBu NH CBr 1 tBuNH CBr 2 CF₃ NH CBr 0 CF₃ NH CBr 1 CF₃ NH CBr 2

TABLE 10 R¹ A¹ A³ n CH₂CF₃ NH CBr 0 CH₂CF₃ NH CBr 1 CH₂CF₃ NH CBr 2CH═CH₂ NH CBr 0 CH═CH₂ NH CBr 1 CH═CH₂ NH CBr 2 CH₂CH═CH₂ NH CBr 0CH₂CH═CH₂ NH CBr 1 CH₂CH═CH₂ NH CBr 2 C≡CH NH CBr 0 C≡CH NH CBr 1 C≡CHNH CBr 2 CH₂C≡CH NH CBr 0 CH₂C≡CH NH CBr 1 CH₂C≡CH NH CBr 2 CycPr NH CBr0 CycPr NH CBr 1 CycPr NH CBr 2 CH₂CycPr NH CBr 0 CH₂CycPr NH CBr 1CH₂CycPr NH CBr 2

TABLE 11 R¹ A¹ A³ n Me N(CH₂OMe) N 0 Me N(CH₂OMe) N 1 Me N(CH₂OMe) N 2Et N(CH₂OMe) N 0 Et N(CH₂OMe) N 1 Et N(CH₂OMe) N 2 Pr N(CH₂OMe) N 0 PrN(CH₂OMe) N 1 Pr N(CH₂OMe) N 2 iPr N(CH₂OMe) N 0 iPr N(CH₂OMe) N 1 iPrN(CH₂OMe) N 2 tBu N(CH₂OMe) N 0 tBu N(CH₂OMe) N 1 tBu N(CH₂OMe) N 2 CF₃N(CH₂OMe) N 0 CF₃ N(CH₂OMe) N 1 CF₃ N(CH₂OMe) N 2 CH₂CF₃ N(CH₂OMe) N 0CH₂CF₃ N(CH₂OMe) N 1 CH₂CF₃ N(CH₂OMe) N 2 CH═CH₂ N(CH₂OMe) N 0 CH═CH₂N(CH₂OMe) N 1 CH═CH₂ N(CH₂OMe) N 2

TABLE 12 R¹ A¹ A³ n CH₂CH═CH₂ N(CH₂OMe) N 0 CH₂CH═CH₂ N(CH₂OMe) N 1CH₂CH═CH₂ N(CH₂OMe) N 2 C≡CH N(CH₂OMe) N 0 C≡CH N(CH₂OMe) N 1 C≡CHN(CH₂OMe) N 2 CH₂C≡CH N(CH₂OMe) N 0 CH₂C≡CH N(CH₂OMe) N 1 CH₂C≡CHN(CH₂OMe) N 2 CycPr N(CH₂OMe) N 0 CycPr N(CH₂OMe) N 1 CycPr N(CH₂OMe) N2 CH₂CycPr N(CH₂OMe) N 0 CH₂CycPr N(CH₂OMe) N 1 CH₂CycPr N(CH₂OMe) N 2Me N(CH₂OMe) CH 0 Me N(CH₂OMe) CH 1 Me N(CH₂OMe) CH 2 Et N(CH₂OMe) CH 0Et N(CH₂OMe) CH 1 Et N(CH₂OMe) CH 2 Pr N(CH₂OMe) CH 0 Pr N(CH₂OMe) CH 1Pr N(CH₂OMe) CH 2

TABLE 13 R¹ A¹ A³ n iPr N(CH₂OMe) CH 0 iPr N(CH₂OMe) CH 1 iPr N(CH₂OMe)CH 2 tBu N(CH₂OMe) CH 0 tBu N(CH₂OMe) CH 1 tBu N(CH₂OMe) CH 2 CF₃N(CH₂OMe) CH 0 CF₃ N(CH₂OMe) CH 1 CF₃ N(CH₂OMe) CH 2 CH₂CF₃ N(CH₂OMe) CH0 CH₂CF₃ N(CH₂OMe) CH 1 CH₂CF₃ N(CH₂OMe) CH 2 CH═CH₂ N(CH₂OMe) CH 0CH═CH₂ N(CH₂OMe) CH 1 CH═CH₂ N(CH₂OMe) CH 2 CH₂CH═CH₂ N(CH₂OMe) CH 0CH₂CH═CH₂ N(CH₂OMe) CH 1 CH₂CH═CH₂ N(CH₂OMe) CH 2 C≡CH N(CH₂OMe) CH 0C≡CH N(CH₂OMe) CH 1 C≡CH N(CH₂OMe) CH 2 CH₂C≡CH N(CH₂OMe) CH 0 CH₂C≡CHN(CH₂OMe) CH 1 CH₂C≡CH N(CH₂OMe) CH 2

TABLE 14 R¹ A¹ A³ n CycPr N(CH₂OMe) CH 0 CycPr N(CH₂OMe) CH 1 CycPrN(CH₂OMe) CH 2 CH₂CycPr N(CH₂OMe) CH 0 CH₂CycPr N(CH₂OMe) CH 1 CH₂CycPrN(CH₂OMe) CH 2 Me N(CH₂OMe) CBr 0 Me N(CH₂OMe) CBr 1 Me N(CH₂OMe) CBr 2Et N(CH₂OMe) CBr 0 Et N(CH₂OMe) CBr 1 Et N(CH₂OMe) CBr 2 Pr N(CH₂OMe)CBr 0 Pr N(CH₂OMe) CBr 1 Pr N(CH₂OMe) CBr 2 iPr N(CH₂OMe) CBr 0 iPrN(CH₂OMe) CBr 1 iPr N(CH₂OMe) CBr 2 tBu N(CH₂OMe) CBr 0 tBu N(CH₂OMe)CBr 1 tBu N(CH₂OMe) CBr 2 CF₃ N(CH₂OMe) CBr 0 CF₃ N(CH₂OMe) CBr 1 CF₃N(CH₂OMe) CBr 2

TABLE 15 R¹ A¹ A³ n CH₂CF₃ N(CH₂OMe) CBr 0 CH₂CF₃ N(CH₂OMe) CBr 1 CH₂CF₃N(CH₂OMe) CBr 2 CH═CH₂ N(CH₂OMe) CBr 0 CH═CH₂ N(CH₂OMe) CBr 1 CH═CH₂N(CH₂OMe) CBr 2 CH₂CH═CH₂ N(CH₂OMe) CBr 0 CH₂CH═CH₂ N(CH₂OMe) CBr 1CH₂CH═CH₂ N(CH₂OMe) CBr 2 C≡CH N(CH₂OMe) CBr 0 C≡CH N(CH₂OMe) CBr 1 C≡CHN(CH₂OMe) CBr 2 CH₂C≡CH N(CH₂OMe) CBr 0 CH₂C≡CH N(CH₂OMe) CBr 1 CH₂C≡CHN(CH₂OMe) CBr 2 CycPr N(CH₂OMe) CBr 0 CycPr N(CH₂OMe) CBr 1 CycPrN(CH₂OMe) CBr 2 CH₂CycPr N(CH₂OMe) CBr 0 CH₂CycPr N(CH₂OMe) CBr 1CH₂CycPr N(CH₂OMe) CBr 2

TABLE 16 R¹ A¹ A³ n Me N(CH₂OEt) N 0 Me N(CH₂OEt) N 1 Me N(CH₂OEt) N 2Et N(CH₂OEt) N 0 Et N(CH₂OEt) N 1 Et N(CH₂OEt) N 2 Pr N(CH₂OEt) N 0 PrN(CH₂OEt) N 1 Pr N(CH₂OEt) N 2 iPr N(CH₂OEt) N 0 iPr N(CH₂OEt) N 1 iPrN(CH₂OEt) N 2 tBu N(CH₂OEt) N 0 tBu N(CH₂OEt) N 1 tBu N(CH₂OEt) N 2 CF₃N(CH₂OEt) N 0 CF₃ N(CH₂OEt) N 1 CF₃ N(CH₂OEt) N 2 CH₂CF₃ N(CH₂OEt) N 0CH₂CF₃ N(CH₂OEt) N 1 CH₂CF₃ N(CH₂OEt) N 2 CH═CH₂ N(CH₂OEt) N 0 CH═CH₂N(CH₂OEt) N 1 CH═CH₂ N(CH₂OEt) N 2

TABLE 17 R¹ A¹ A³ n CH₂CH═CH₂ N(CH₂OEt) N 0 CH₂CH═CH₂ N(CH₂OEt) N 1CH₂CH═CH₂ N(CH₂OEt) N 2 C≡CH N(CH₂OEt) N 0 C≡CH N(CH₂OEt) N 1 C≡CHN(CH₂OEt) N 2 CH₂C≡CH N(CH₂OEt) N 0 CH₂C≡CH N(CH₂OEt) N 1 CH₂C≡CHN(CH₂OEt) N 2 CycPr N(CH₂OEt) N 0 CycPr N(CH₂OEt) N 1 CycPr N(CH₂OEt) N2 CH₂CycPr N(CH₂OEt) N 0 CH₂CycPr N(CH₂OEt) N 1 CH₂CycPr N(CH₂OEt) N 2Me N(CH₂OEt) CH 0 Me N(CH₂OEt) CH 1 Me N(CH₂OEt) CH 2 Et N(CH₂OEt) CH 0Et N(CH₂OEt) CH 1 Et N(CH₂OEt) CH 2 Pr N(CH₂OEt) CH 0 Pr N(CH₂OEt) CH 1Pr N(CH₂OEt) CH 2

TABLE 18 R¹ A¹ A³ n iPr N(CH₂OEt) CH 0 iPr N(CH₂OEt) CH 1 iPr N(CH₂OEt)CH 2 tBu N(CH₂OEt) CH 0 tBu N(CH₂OEt) CH 1 tBu N(CH₂OEt) CH 2 CF₃N(CH₂OEt) CH 0 CF₃ N(CH₂OEt) CH 1 CF₃ N(CH₂OEt) CH 2 CH₂CF₃ N(CH₂OEt) CH0 CH₂CF₃ N(CH₂OEt) CH 1 CH₂CF₃ N(CH₂OEt) CH 2 CH═CH₂ N(CH₂OEt) CH 0CH═CH₂ N(CH₂OEt) CH 1 CH═CH₂ N(CH₂OEt) CH 2 CH₂CH═CH₂ N(CH₂OEt) CH 0CH₂CH═CH₂ N(CH₂OEt) CH 1 CH₂CH═CH₂ N(CH₂OEt) CH 2 C≡CH N(CH₂OEt) CH 0C≡CH N(CH₂OEt) CH 1 C≡CH N(CH₂OEt) CH 2 CH₂C≡CH N(CH₂OEt) CH 0 CH₂C≡CHN(CH₂OEt) CH 1 CH₂C≡CH N(CH₂OEt) CH 2

TABLE 19 R¹ A¹ A³ n CycPr N(CH₂OEt) CH 0 CycPr N(CH₂OEt) CH 1 CycPrN(CH₂OEt) CH 2 CH₂CycPr N(CH₂OEt) CH 0 CH₂CycPr N(CH₂OEt) CH 1 CH₂CycPrN(CH₂OEt) CH 2 Me N(CH₂OEt) CBr 0 Me N(CH₂OEt) CBr 1 Me N(CH₂OEt) CBr 2Et N(CH₂OEt) CBr 0 Et N(CH₂OEt) CBr 1 Et N(CH₂OEt) CBr 2 Pr N(CH₂OEt)CBr 0 Pr N(CH₂OEt) CBr 1 Pr N(CH₂OEt) CBr 2 iPr N(CH₂OEt) CBr 0 iPrN(CH₂OEt) CBr 1 iPr N(CH₂OEt) CBr 2 tBu N(CH₂OEt) CBr 0 tBu N(CH₂OEt)CBr 1 tBu N(CH₂OEt) CBr 2 CF₃ N(CH₂OEt) CBr 0 CF₃ N(CH₂OEt) CBr 1 CF₃N(CH₂OEt) CBr 2

TABLE 20 R¹ A¹ A³ n CH₂CF₃ N(CH₂OEt) CBr 0 CH₂CF₃ N(CH₂OEt) CBr 1 CH₂CF₃N(CH₂OEt) CBr 2 CH═CH₂ N(CH₂OEt) CBr 0 CH═CH₂ N(CH₂OEt) CBr 1 CH═CH₂N(CH₂OEt) CBr 2 CH₂CH═CH₂ N(CH₂OEt) CBr 0 CH₂CH═CH₂ N(CH₂OEt) CBr 1CH₂CH═CH₂ N(CH₂OEt) CBr 2 C≡CH N(CH₂OEt) CBr 0 C≡CH N(CH₂OEt) CBr 1 C≡CHN(CH₂OEt) CBr 2 CH₂C≡CH N(CH₂OEt) CBr 0 CH₂C≡CH N(CH₂OEt) CBr 1 CH₂C≡CHN(CH₂OEt) CBr 2 CycPr N(CH₂OEt) CBr 0 CycPr N(CH₂OEt) CBr 1 CycPrN(CH₂OEt) CBr 2 CH₂CycPr N(CH₂OEt) CBr 0 CH₂CycPr N(CH₂OEt) CBr 1CH₂CycPr N(CH₂OEt) CBr 2

TABLE 21 R¹ A¹ A³ n Me N(CH₂C≡CH) N 0 Me N(CH₂C≡CH) N 1 Me N(CH₂C≡CH) N2 Et N(CH₂C≡CH) N 0 Et N(CH₂C≡CH) N 1 Et N(CH₂C≡CH) N 2 Pr N(CH₂C≡CH) N0 Pr N(CH₂C≡CH) N 1 Pr N(CH₂C≡CH) N 2 iPr N(CH₂C≡CH) N 0 iPr N(CH₂C≡CH)N 1 iPr N(CH₂C≡CH) N 2 tBu N(CH₂C≡CH) N 0 tBu N(CH₂C≡CH) N 1 tBuN(CH₂C≡CH) N 2 CF₃ N(CH₂C≡CH) N 0 CF₃ N(CH₂C≡CH) N 1 CF₃ N(CH₂C≡CH) N 2CH₂CF₃ N(CH₂C≡CH) N 0 CH₂CF₃ N(CH₂C≡CH) N 1 CH₂CF₃ N(CH₂C≡CH) N 2 CH═CH₂N(CH₂C≡CH) N 0 CH═CH₂ N(CH₂C≡CH) N 1 CH═CH₂ N(CH₂C≡CH) N 2

TABLE 22 R¹ A¹ A³ n CH₂CH═CH₂ N(CH₂C≡CH) N 0 CH₂CH═CH₂ N(CH₂C≡CH) N 1CH₂CH═CH₂ N(CH₂C≡CH) N 2 C≡CH N(CH₂C≡CH) N 0 C≡CH N(CH₂C≡CH) N 1 C≡CHN(CH₂C≡CH) N 2 CH₂C≡CH N(CH₂C≡CH) N 0 CH₂C≡CH N(CH₂C≡CH) N 1 CH₂C≡CHN(CH₂C≡CH) N 2 CycPr N(CH₂C≡CH) N 0 CycPr N(CH₂C≡CH) N 1 CycPrN(CH₂C≡CH) N 2 CH₂CycPr N(CH₂C≡CH) N 0 CH₂CycPr N(CH₂C≡CH) N 1 CH₂CycPrN(CH₂C≡CH) N 2 Me N(CH₂C≡CH) CH 0 Me N(CH₂C≡CH) CH 1 Me N(CH₂C≡CH) CH 2Et N(CH₂C≡CH) CH 0 Et N(CH₂C≡CH) CH 1 Et N(CH₂C≡CH) CH 2 Pr N(CH₂C≡CH)CH 0 Pr N(CH₂C≡CH) CH 1 Pr N(CH₂C≡CH) CH 2

TABLE 23 R¹ A¹ A³ n iPr N(CH₂C≡CH) CH 0 iPr N(CH₂C≡CH) CH 1 iPrN(CH₂C≡CH) CH 2 tBu N(CH₂C≡CH) CH 0 tBu N(CH₂C≡CH) CH 1 tBu N(CH₂C≡CH)CH 2 CF₃ N(CH₂C≡CH) CH 0 CF₃ N(CH₂C≡CH) CH 1 CF₃ N(CH₂C≡CH) CH 2 CH₂CF₃N(CH₂C≡CH) CH 0 CH₂CF₃ N(CH₂C≡CH) CH 1 CH₂CF₃ N(CH₂C≡CH) CH 2 CH═CH₂N(CH₂C≡CH) CH 0 CH═CH₂ N(CH₂C≡CH) CH 1 CH═CH₂ N(CH₂C≡CH) CH 2 CH₂CH═CH₂N(CH₂C≡CH) CH 0 CH₂CH═CH₂ N(CH₂C≡CH) CH 1 CH₂CH═CH₂ N(CH₂C≡CH) CH 2 C≡CHN(CH₂C≡CH) CH 0 C≡CH N(CH₂C≡CH) CH 1 C≡CH N(CH₂C≡CH) CH 2 CH₂C≡CHN(CH₂C≡CH) CH 0 CH₂C≡CH N(CH₂C≡CH) CH 1 CH₂C≡CH N(CH₂C≡CH) CH 2

TABLE 24 R¹ A¹ A³ n CycPr N(CH₂C≡CH) CH 0 CycPr N(CH₂C≡CH) CH 1 CycPrN(CH₂C≡CH) CH 2 CH₂CycPr N(CH₂C≡CH) CH 0 CH₂CycPr N(CH₂C≡CH) CH 1CH₂CycPr N(CH₂C≡CH) CH 2 Me N(CH₂C≡CH) CBr 0 Me N(CH₂C≡CH) CBr 1 MeN(CH₂C≡CH) CBr 2 Et N(CH₂C≡CH) CBr 0 Et N(CH₂C≡CH) CBr 1 Et N(CH₂C≡CH)CBr 2 Pr N(CH₂C≡CH) CBr 0 Pr N(CH₂C≡CH) CBr 1 Pr N(CH₂C≡CH) CBr 2 iPrN(CH₂C≡CH) CBr 0 iPr N(CH₂C≡CH) CBr 1 iPr N(CH₂C≡CH) CBr 2 tBuN(CH₂C≡CH) CBr 0 tBu N(CH₂C≡CH) CBr 1 tBu N(CH₂C≡CH) CBr 2 CF₃N(CH₂C≡CH) CBr 0 CF₃ N(CH₂C≡CH) CBr 1 CF₃ N(CH₂C≡CH) CBr 2

TABLE 25 R¹ A¹ A³ n CH₂CF₃ N(CH₂C≡CH) CBr 0 CH₂CF₃ N(CH₂C≡CH) CBr 1CH₂CF₃ N(CH₂C≡CH) CBr 2 CH═CH₂ N(CH₂C≡CH) CBr 0 CH═CH₂ N(CH₂C≡CH) CBr 1CH═CH₂ N(CH₂C≡CH) CBr 2 CH₂CH═CH₂ N(CH₂C≡CH) CBr 0 CH₂CH═CH₂ N(CH₂C≡CH)CBr 1 CH₂CH═CH₂ N(CH₂C≡CH) CBr 2 C≡CH N(CH₂C≡CH) CBr 0 C≡CH N(CH₂C≡CH)CBr 1 C≡CH N(CH₂C≡CH) CBr 2 CH₂C≡CH N(CH₂C≡CH) CBr 0 CH₂C≡CH N(CH₂C≡CH)CBr 1 CH₂C≡CH N(CH₂C≡CH) CBr 2 CycPr N(CH₂C≡CH) CBr 0 CycPr N(CH₂C≡CH)CBr 1 CycPr N(CH₂C≡CH) CBr 2 CH₂CycPr N(CH₂C≡CH) CBr 0 CH₂CycPrN(CH₂C≡CH) CBr 1 CH₂CycPr N(CH₂C≡CH) CBr 2

TABLE 26 R¹ A¹ A³ n Me O N 0 Me O N 1 Me O N 2 Et O N 0 Et O N 1 Et O N2 Pr O N 0 Pr O N 1 Pr O N 2 iPr O N 0 iPr O N 1 iPr O N 2 tBu O N 0 tBuO N 1 tBu O N 2 CF₃ O N 0 CF₃ O N 1 CF₃ O N 2 CH₂CF₃ O N 0 CH₂CF₃ O N 1CH₂CF₃ O N 2 CH═CH₂ O N 0 CH═CH₂ O N 1 CH═CH₂ O N 2

TABLE 27 R¹ A¹ A³ n CH₂CH═CH₂ O N 0 CH₂CH═CH₂ O N 1 CH₂CH═CH₂ O N 2 C≡CHO N 0 C≡CH O N 1 C≡CH O N 2 CH₂C≡CH O N 0 CH₂C≡CH O N 1 CH₂C≡CH O N 2CycPr O N 0 CycPr O N 1 CycPr O N 2 CH₂CycPr O N 0 CH₂CycPr O N 1CH₂CycPr O N 2 Me O CH 0 Me O CH 1 Me O CH 2 Et O CH 0 Et O CH 1 Et O CH2 Pr O CH 0 Pr O CH 1 Pr O CH 2

TABLE 28 R¹ A¹ A³ n iPr O CH 0 iPr O CH 1 iPr O CH 2 tBu O CH 0 tBu O CH1 tBu O CH 2 CF₃ O CH 0 CF₃ O CH 1 CF₃ O CH 2 CH₂CF₃ O CH 0 CH₂CF₃ O CH1 CH₂CF₃ O CH 2 CH═CH₂ O CH 0 CH═CH₂ O CH 1 CH═CH₂ O CH 2 CH₂CH═CH₂ O CH0 CH₂CH═CH₂ O CH 1 CH₂CH═CH₂ O CH 2 C≡CH O CH 0 C≡CH O CH 1 C≡CH O CH 2CH₂C≡CH O CH 0 CH₂C≡CH O CH 1 CH₂C≡CH O CH 2

TABLE 29 R¹ A¹ A³ n CycPr O CH 0 CycPr O CH 1 CycPr O CH 2 CH₂CycPr O CH0 CH₂CycPr O CH 1 CH₂CycPr O CH 2 Me O CBr 0 Me O CBr 1 Me O CBr 2 Et OCBr 0 Et O CBr 1 Et O CBr 2 Pr O CBr 0 Pr O CBr 1 Pr O CBr 2 iPr O CBr 0iPr O CBr 1 iPr O CBr 2 tBu O CBr 0 tBu O CBr 1 tBu O CBr 2 CF₃ O CBr 0CF₃ O CBr 1 CF₃ O CBr 2

TABLE 30 R¹ A¹ A³ n CH₂CF₃ O CBr 0 CH₂CF₃ O CBr 1 CH₂CF₃ O CBr 2 CH═CH₂O CBr 0 CH═CH₂ O CBr 1 CH═CH₂ O CBr 2 CH₂CH═CH₂ O CBr 0 CH₂CH═CH₂ O CBr1 CH₂CH═CH₂ O CBr 2 C≡CH O CBr 0 C≡CH O CBr 1 C≡CH O CBr 2 CH₂C≡CH O CBr0 CH₂C≡CH O CBr 1 CH₂C≡CH O CBr 2 CycPr O CBr 0 CycPr O CBr 1 CycPr OCBr 2 CH₂CycPr O CBr 0 CH₂CycPr O CBr 1 CH₂CycPr O CBr 2

TABLE 31 R¹ A¹ A³ n Me S N 0 Me S N 1 Me S N 2 Et S N 0 Et S N 1 Et S N2 Pr S N 0 Pr S N 1 Pr S N 2 iPr S N 0 iPr S N 1 iPr S N 2 tBu S N 0 tBuS N 1 tBu S N 2 CF₃ S N 0 CF₃ S N 1 CF₃ S N 2 CH₂CF₃ S N 0 CH₂CF₃ S N 1CH₂CF₃ S N 2 CH═CH₂ S N 0 CH═CH₂ S N 1 CH═CH₂ S N 2

TABLE 32 R¹ A¹ A³ n CH₂CH═CH₂ S N 0 CH₂CH═CH₂ S N 1 CH₂CH═CH₂ S N 2 C≡CHS N 0 C≡CH S N 1 C≡CH S N 2 CH₂C≡CH S N 0 CH₂C≡CH S N 1 CH₂C≡CH S N 2CycPr S N 0 CycPr S N 1 CycPr S N 2 CH₂CycPr S N 0 CH₂CycPr S N 1CH₂CycPr S N 2 Me S CH 0 Me S CH 1 Me S CH 2 Et S CH 0 Et S CH 1 Et S CH2 Pr S CH 0 Pr S CH 1 Pr S CH 2

TABLE 33 R¹ A¹ A³ n iPr S CH 0 iPr S CH 1 iPr S CH 2 tBu S CH 0 tBu S CH1 tBu S CH 2 CF₃ S CH 0 CF₃ S CH 1 CF₃ S CH 2 CH₂CF₃ S CH 0 CH₂CF₃ S CH1 CH₂CF₃ S CH 2 CH═CH₂ S CH 0 CH═CH₂ S CH 1 CH═CH₂ S CH 2 CH₂CH═CH₂ S CH0 CH₂CH═CH₂ S CH 1 CH₂CH═CH₂ S CH 2 C≡CH S CH 0 C≡CH S CH 1 C≡CH S CH 2CH₂C≡CH S CH 0 CH₂C≡CH S CH 1 CH₂C≡CH S CH 2

TABLE 34 R¹ A¹ A³ n CycPr S CH 0 CycPr S CH 1 CycPr S CH 2 CH₂CycPr S CH0 CH₂CycPr S CH 1 CH₂CycPr S CH 2 Me S CBr 0 Me S CBr 1 Me S CBr 2 Et SCBr 0 Et S CBr 1 Et S CBr 2 Pr S CBr 0 Pr S CBr 1 Pr S CBr 2 iPr S CBr 0iPr S CBr 1 iPr S CBr 2 tBu S CBr 0 tBu S CBr 1 tBu S CBr 2 CF₃ S CBr 0CF₃ S CBr 1 CF₃ S CBr 2

TABLE 35 R¹ A¹ A³ n CH₂CF₃ S CBr 0 CH₂CF₃ S CBr 1 CH₂CF₃ S CBr 2 CH═CH₂S CBr 0 CH═CH₂ S CBr 1 CH═CH₂ S CBr 2 CH₂CH═CH₂ S CBr 0 CH₂CH═CH₂ S CBr1 CH₂CH═CH₂ S CBr 2 C≡CH S CBr 0 C≡CH S CBr 1 C≡CH S CBr 2 CH₂C≡CH S CBr0 CH₂C≡CH S CBr 1 CH₂C≡CH S CBr 2 CycPr S CBr 0 CycPr S CBr 1 CycPr SCBr 2 CH₂CycPr S CBr 0 CH₂CycPr S CBr 1 CH₂CycPr S CBr 2

In the above [Table 1] to [Table 35], Me represents a methyl group, Etrepresents an ethyl group, Pr represents a n-propyl group, iPrrepresents isopropyl group, tBu represents a tert-butyl group, and CycPrrepresents cyclopropyl group.

A compound represented by the formula (A) wherein R² is a fluorine atom,R³ and R⁴ are independently a hydrogen atom, R⁵ is a trifluoromethylgroup, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a fluorine atom,R² and R⁴ are independently a hydrogen atom, R⁵ is a trifluoromethylgroup, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is a fluorine atom,R² and R³ are independently a hydrogen atom, R⁵ is a trifluoromethylgroup, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R² is a chlorine atom,R³ and R⁴ are independently a hydrogen atom, R⁵ is a trifluoromethylgroup, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a chlorine atom,R² and R⁴ are independently a hydrogen atom, R⁵ is a trifluoromethylgroup, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is a chlorine atom,R² and R³ are independently a hydrogen atom, R⁵ is a trifluoromethylgroup, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R² is a bromine atom,R³ and R⁴ are independently a hydrogen atom, R⁵ is a trifluoromethylgroup, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a bromine atom,R² and R⁴ are independently a hydrogen atom, R⁵ is a trifluoromethylgroup, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is a bromine atom,R² and R³ are independently a hydrogen atom, R⁵ is a trifluoromethylgroup, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R² is a methyl group,R³ and R⁴ are independently a hydrogen atom, R⁵ is a trifluoromethylgroup, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a methyl group,R² and R⁴ are independently a hydrogen atom, R⁵ is a trifluoromethylgroup, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is a methyl group,R² and R³ are independently a hydrogen atom, R⁵ is a trifluoromethylgroup, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R² is atrifluoromethyl group, R³ and R⁴ are independently a hydrogen atom, R⁵is a trifluoromethyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is atrifluoromethyl group, R² and R⁴ are independently a hydrogen atom, R⁵is a trifluoromethyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is atrifluoromethyl group, R² and R⁴ are independently a hydrogen atom, R⁵is a trifluoromethyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is apentafluoroethyl group, R² and R⁴ are independently a hydrogen atom, R⁵is a trifluoromethyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is atrifluoromethoxy group, R² and R⁴ are independently a hydrogen atom, R⁵is a trifluoromethyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a 2-pyridylgroup, R² and R⁴ are independently a hydrogen atom, R⁵ is atrifluoromethyl group, and R¹, A¹, A³ and n represent any one of thecombinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a3-chloro-2-pyridyl group, R² and R⁴ are independently a hydrogen atom,R⁵ is a trifluoromethyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a 2-pyrimidinylgroup, R² and R⁴ are independently a hydrogen atom, R⁵ is atrifluoromethyl group, and R¹, A¹, A³ and n represent any one of thecombinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is —SF₅, R² and R⁴are independently a hydrogen atom, R⁵ is a trifluoromethyl group, andR¹, A¹, A³ and n represent any one of the combinations as listed in[Table 1] to [Table 35].

A compound represented by the formula (A) wherein R², R³ and R⁴ areindependently a hydrogen atom, R⁵ is a pentafluoroethyl group, and R¹,A¹, A³ and n represent any one of the combinations as listed in [Table1] to [Table 35].

A compound represented by the formula (A) wherein R² is a fluorine atom,R³ and R⁴ are independently a hydrogen atom, R⁵ is a pentafluoroethylgroup, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a fluorine atom,R² and R⁴ are independently a hydrogen atom, R⁵ is a pentafluoroethylgroup, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is a fluorine atom,R² and R³ are independently a hydrogen atom, R⁵ is a pentafluoroethylgroup, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R² is a chlorine atom,R³ and R⁴ are independently a hydrogen atom, R⁵ is a pentafluoroethylgroup, R¹, A¹, A³ and n represent any one of the combinations as listedin [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a chlorine atom,R² and R⁴ are independently a hydrogen atom, R⁵ is a pentafluoroethylgroup, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is a chlorine atom,R² and R³ are independently a hydrogen atom, R⁵ is a pentafluoroethylgroup, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R² is a bromine atom,R³ and R⁴ are independently a hydrogen atom, R⁵ is a pentafluoroethylgroup, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a bromine atom,R² and R⁴ are independently a hydrogen atom, R⁵ is a pentafluoroethylgroup, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is a bromine atom,R² and R³ are independently a hydrogen atom, R⁵ is a pentafluoroethylgroup, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R² is a methyl group,R³ and R⁴ are independently a hydrogen atom, R⁵ is a pentafluoroethylgroup, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a methyl group,R² and R⁴ are independently a hydrogen atom, R⁵ is a pentafluoroethylgroup, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is a methyl group,R² and R³ are independently a hydrogen atom, R⁵ is a pentafluoroethylgroup, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R² is atrifluoromethyl group, R³ and R⁴ are independently a hydrogen atom, R⁵is a pentafluoroethyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is atrifluoromethyl group, R² and R⁴ are independently a hydrogen atom, R⁵is a pentafluoroethyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is atrifluoromethyl group, R² and R³ are independently a hydrogen atom, R⁵is a pentafluoroethyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is apentafluoroethyl group, R² and R⁴ are independently a hydrogen atom, R⁵is a pentafluoroethyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is atrifluoromethoxy group, R² and R⁴ are independently a hydrogen atom, R⁵is a pentafluoroethyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a 2-pyridylgroup, R² and R⁴ are independently a hydrogen atom, R⁵ is apentafluoroethyl group, and R¹, A¹, A³ and n represent any one of thecombinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a3-chloro-2-pyridyl group, R² and R⁴ are independently a hydrogen atom,R⁵ is a pentafluoroethyl group, and R¹, A¹, A³ and n represent any oneof the combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a 2-pyrimidinylgroup, R² and R⁴ are independently a hydrogen atom, R⁵ is apentafluoroethyl group, and R¹, A¹, A³ and n represent any one of thecombinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is —SF₅, R² and R⁴are independently a hydrogen atom, R⁵ is a pentafluoroethyl group, andR¹, A¹, A³ and n represent any one of the combinations as listed in[Table 1] to [Table 35].

A compound represented by the formula (A) wherein R², R³ and R⁴ areindependently a hydrogen atom, R⁵ is a heptafluoroisopropyl group, andR¹, A¹, A³ and n represent any one of the combinations as listed in[Table 1] to [Table 35].

A compound represented by the formula (A) wherein R² is a fluorine atom,R³ and R⁴ are independently a hydrogen atom, R⁵ is aheptafluoroisopropyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a fluorine atom,R² and R⁴ are independently a hydrogen atom, R⁵ is aheptafluoroisopropyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is a fluorine atom,R² and R³ are independently a hydrogen atom, R⁵ is aheptafluoroisopropyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R² is a chlorine atom,R³ and R⁴ are independently a hydrogen atom, R⁵ is aheptafluoroisopropyl group, R¹, A¹, A³ and n represent any one of thecombinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a chlorine atom,R² and R⁴ are independently a hydrogen atom, R⁵ is aheptafluoroisopropyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is a chlorine atom,R² and R³ are independently a hydrogen atom, R⁵ is aheptafluoroisopropyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R² is a bromine atom,R³ and R⁴ are independently a hydrogen atom, R⁵ is aheptafluoroisopropyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a bromine atom,R² and R⁴ are independently a hydrogen atom, R⁵ is aheptafluoroisopropyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is a bromine atom,R² and R³ are independently a hydrogen atom, R⁵ is aheptafluoroisopropyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R² is a methyl group,R³ and R⁴ are independently a hydrogen atom, R⁵ is aheptafluoroisopropyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a methyl group,R² and R⁴ are independently a hydrogen atom, R⁵ is aheptafluoroisopropyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is a methyl group,R² and R³ are independently a hydrogen atom, R⁵ is aheptafluoroisopropyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R² is atrifluoromethyl group, R³ and R⁴ are independently a hydrogen atom, R⁵is a heptafluoroisopropyl group, and R¹, A¹, A³ and n represent any oneof the combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is atrifluoromethyl group, R² and R⁴ are independently a hydrogen atom, R⁵is a heptafluoroisopropyl group, and R¹, A¹, A³ and n represent any oneof the combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is atrifluoromethyl group, R² and R³ are independently a hydrogen atom, R⁵is a heptafluoroisopropyl group, and R¹, A¹, A³ and n represent any oneof the combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is apentafluoroethyl group, R² and R⁴ are independently a hydrogen atom, R⁵is a heptafluoroisopropyl group, and R¹, A¹, A³ and n represent any oneof the combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is atrifluoromethoxy group, R² and R⁴ are independently a hydrogen atom, R⁵is a heptafluoroisopropyl group, and R¹, A¹, A³ and n represent any oneof the combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a 2-pyridylgroup, R² and R⁴ are independently a hydrogen atom, R⁵ is aheptafluoroisopropyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a3-chloro-2-pyridyl group, R² and R⁴ are independently a hydrogen atom,R⁵ is a heptafluoroisopropyl group, and R¹, A¹, A³ and n represent anyone of the combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a 2-pyrimidinylgroup, R² and R⁴ are independently a hydrogen atom, R⁵ is aheptafluoroisopropyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is —SF₅, R² and R⁴are independently a hydrogen atom, R⁵ is a heptafluoroisopropyl group,and R¹, A¹, A³ and n represent any one of the combinations as listed in[Table 1] to [Table 35].

A compound represented by the formula (A) wherein R², R³ and R⁴ areindependently a hydrogen atom, R⁵ is a trifluoromethoxy group, and R¹,A¹, A³ and n represent any one of the combinations as listed in [Table1] to [Table 35].

A compound represented by the formula (A) wherein R² is a fluorine atom,R³ and R⁴ are independently a hydrogen atom, R⁵ is a trifluoromethoxygroup, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a fluorine atom,R² and R⁴ are independently a hydrogen atom, R⁵ is a trifluoromethoxygroup, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is a fluorine atom,R² and R³ are independently a hydrogen atom, R⁵ is a trifluoromethoxygroup, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R² is a chlorine atom,R³ and R⁴ are independently a hydrogen atom, R⁵ is a trifluoromethoxygroup, R¹, A¹, A³ and n represent any one of the combinations as listedin [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a chlorine atom,R² and R⁴ are independently a hydrogen atom, R⁵ is a trifluoromethoxygroup, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is a chlorine atom,R² and R³ are independently a hydrogen atom, R⁵ is a trifluoromethoxygroup, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R² is a bromine atom,R³ and R⁴ are independently a hydrogen atom, R⁵ is a trifluoromethoxygroup, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a bromine atom,R² and R⁴ are independently a hydrogen atom, R⁵ is a trifluoromethoxygroup, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is a bromine atom,R² and R³ are independently a hydrogen atom, R⁵ is a trifluoromethoxygroup, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R² is a methyl group,R³ and R⁴ are independently a hydrogen atom, R⁵ is a trifluoromethoxygroup, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a methyl group,R² and R⁴ are independently a hydrogen atom, R⁵ is a trifluoromethoxygroup, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is a methyl group,R² and R³ are independently a hydrogen atom, R⁵ is a trifluoromethoxygroup, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R² is atrifluoromethyl group, R³ and R⁴ are independently a hydrogen atom, R⁵is a trifluoromethoxy group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is atrifluoromethyl group, R² and R⁴ are independently a hydrogen atom, R⁵is a trifluoromethoxy group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is atrifluoromethyl group, R² and R³ are independently a hydrogen atom, R⁵is a trifluoromethoxy group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is apentafluoroethyl group, R² and R⁴ are independently a hydrogen atom, R⁵is a trifluoromethoxy group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is atrifluoromethoxy group, R² and R⁴ are independently a hydrogen atom, R⁵is a trifluoromethoxy group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a 2-pyridylgroup, R² and R⁴ are independently a hydrogen atom, R⁵ is atrifluoromethoxy group, and R¹, A¹, A³ and n represent any one of thecombinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a3-chloro-2-pyridyl group, R² and R⁴ are independently a hydrogen atom,R⁵ is a trifluoromethoxy group, and R¹, A¹, A³ and n represent any oneof the combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a 2-pyrimidinylgroup, R² and R⁴ are independently a hydrogen atom, R⁵ is atrifluoromethoxy group, and R¹, A¹, A³ and n represent any one of thecombinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is —SF₅, R² and R⁴are independently a hydrogen atom, R⁵ is a trifluoromethoxy group, andR¹, A¹, A³ and n represent any one of the combinations as listed in[Table 1] to [Table 35].

A compound represented by the formula (A) wherein R², R³ and R⁴ areindependently a hydrogen atom, R⁵ is a trifluoromethylsulfanyl group,and R¹, A¹, A³ and n represent any one of the combinations as listed in[Table 1] to [Table 35].

A compound represented by the formula (A) wherein R² is a fluorine atom,R³ and R⁴ are independently a hydrogen atom, R⁵ is atrifluoromethylsulfanyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a fluorine atom,R² and R⁴ are independently a hydrogen atom, R⁵ is atrifluoromethylsulfanyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is a fluorine atom,R² and R³ are independently a hydrogen atom, R⁵ is atrifluoromethylsulfanyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R² is a chlorine atom,R³ and R⁴ are independently a hydrogen atom, R⁵ is atrifluoromethylsulfanyl group, R¹, A¹, A³ and n represent any one of thecombinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a chlorine atom,R² and R⁴ are independently a hydrogen atom, R⁵ is atrifluoromethylsulfanyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is a chlorine atom,R² and R³ are independently a hydrogen atom, R⁵ is atrifluoromethylsulfanyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R² is a bromine atom,R³ and R⁴ are independently a hydrogen atom, R⁵ is atrifluoromethylsulfanyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a bromine atom,R² and R⁴ are independently a hydrogen atom, R⁵ is atrifluoromethylsulfanyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is a bromine atom,R² and R³ are independently a hydrogen atom, R⁵ is atrifluoromethylsulfanyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R² is a methyl group,R³ and R⁴ are independently a hydrogen atom, R⁵ is atrifluoromethylsulfanyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed, in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a methyl group,R² and R⁴ are independently a hydrogen atom, R⁵ is atrifluoromethylsulfanyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is a methyl group,R² and R³ are independently a hydrogen atom, R⁵ is atrifluoromethylsulfanyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R² is atrifluoromethyl group, R³ and R⁴ are independently a hydrogen atom, R⁵is a trifluoromethylsulfanyl group, and R¹, A¹, A³ and n represent anyone of the combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is atrifluoromethyl group, R² and R⁴ are independently a hydrogen atom, R⁵is a trifluoromethylsulfanyl group, and R¹, A¹, A³ and n represent anyone of the combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is atrifluoromethyl group, R² and R³ are independently a hydrogen atom, R⁵is a trifluoromethylsulfanyl group, and R¹, A¹, A³ and n represent anyone of the combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is apentafluoroethyl group, R² and R⁴ are independently a hydrogen atom, R⁵is a trifluoromethylsulfanyl group, and R¹, A¹, A³ and n represent anyone of the combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is atrifluoromethoxy group, R² and R⁴ are independently a hydrogen atom, R⁵is a trifluoromethylsulfanyl group, and R¹, A¹, A³ and n represent anyone of the combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a 2-pyridylgroup, R² and R⁴ are independently a hydrogen atom, R⁵ is atrifluoromethylsulfanyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a3-chloro-2-pyridyl group, R² and R⁴ are independently a hydrogen atom,R⁵ is a trifluoromethylsulfanyl group, and R¹, A¹, A³ and n representany one of the combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a 2-pyrimidinylgroup, R² and R⁴ are independently a hydrogen atom, R⁵ is atrifluoromethylsulfanyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is —SF₅, R² and R⁴are independently a hydrogen atom, R⁵ is a trifluoromethylsulfanylgroup, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R², R³ and R⁴ areindependently a hydrogen atom, R⁵ is a trifluoromethylsulfinyl group,and R¹, A¹, A³ and n represent any one of the combinations as listed in[Table 1] to [Table 35].

A compound represented by the formula (A) wherein R² is a fluorine atom,R³ and R⁴ are independently a hydrogen atom, R⁵ is atrifluoromethylsulfinyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a fluorine atom,R² and R⁴ are independently a hydrogen atom, R⁵ is atrifluoromethylsulfinyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is a fluorine atom,R² and R³ are independently a hydrogen atom, R⁵ is atrifluoromethylsulfinyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R² is a chlorine atom,R³ and R⁴ are independently a hydrogen atom, R⁵ is atrifluoromethylsulfinyl group, R¹, A¹, A³ and n represent any one of thecombinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a chlorine atom,R² and R⁴ are independently a hydrogen atom, R⁵ is atrifluoromethylsulfinyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is a chlorine atom,R² and R³ are independently a hydrogen atom, R⁵ is atrifluoromethylsulfinyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R² is a bromine atom,R³ and R⁴ are independently a hydrogen atom, R⁵ is atrifluoromethylsulfinyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a bromine atom,R² and R⁴ are independently a hydrogen atom, R⁵ is atrifluoromethylsulfinyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is a bromine atom,R² and R³ are independently a hydrogen atom, R⁵ is atrifluoromethylsulfinyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R² is a methyl group,R³ and R⁴ are independently a hydrogen atom, R⁵ is atrifluoromethylsulfinyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a methyl group,R² and R⁴ are independently a hydrogen atom, R⁵ is atrifluoromethylsulfinyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is a methyl group,R² and R³ are independently a hydrogen atom, R⁵ is atrifluoromethylsulfinyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R² is atrifluoromethyl group, R³ and R⁴ are independently a hydrogen atom, R⁵is a trifluoromethylsulfinyl group, and R¹, A¹, A³ and n represent anyone of the combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is atrifluoromethyl group, R² and R⁴ are independently a hydrogen atom, R⁵is a trifluoromethylsulfinyl group, and R¹, A¹, A³ and n represent anyone of the combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is atrifluoromethyl group, R² and R³ are independently a hydrogen atom, R⁵is a trifluoromethylsulfinyl group, and R¹, A¹, A³ and n represent anyone of the combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is apentafluoroethyl group, R² and R⁴ are independently a hydrogen atom, R⁵is a trifluoromethylsulfinyl group, and R¹, A¹, A³ and n represent anyone of the combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is atrifluoromethoxy group, R² and R⁴ are independently a hydrogen atom, R⁵is a trifluoromethylsulfinyl group, and R¹, A¹, A³ and n represent anyone of the combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a 2-pyridylgroup, R² and R⁴ are independently a hydrogen atom, R⁵ is atrifluoromethylsulfinyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a3-chloro-2-pyridyl group, R² and R⁴ are independently a hydrogen atom,R⁵ is a trifluoromethylsulfinyl group, and R¹, A¹, A³ and n representany one of the combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a 2-pyrimidinylgroup, R² and R⁴ are independently a hydrogen atom, R⁵ is atrifluoromethylsulfinyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is —SF₅, R² and R⁴are independently a hydrogen atom, R⁵ is a trifluoromethylsulfinylgroup, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R², R³ and R⁴ areindependently a hydrogen atom, R⁵ is a trifluoromethylsulfonyl group,and R¹, A¹, A³ and n represent any one of the combinations as listed in[Table 1] to [Table 35].

A compound represented by the formula (A) wherein R² is a fluorine atom,R³ and R⁴ are independently a hydrogen atom, R⁵ is atrifluoromethylsulfonyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a fluorine atom,R² and R⁴ are independently a hydrogen atom, R⁵ is atrifluoromethylsulfonyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is a fluorine atom,R² and R³ are independently a hydrogen atom, R⁵ is atrifluoromethylsulfonyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R² is a chlorine atom,R³ and R⁴ are independently a hydrogen atom, R⁵ is atrifluoromethylsulfonyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a chlorine atom,R² and R⁴ are independently a hydrogen atom, R⁵ is atrifluoromethylsulfonyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is a chlorine atom,R² and R³ are independently a hydrogen atom, R⁵ is atrifluoromethylsulfonyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R² is a bromine atom,R³ and R⁴ are independently a hydrogen atom, R⁵ is atrifluoromethylsulfonyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a bromine atom,R² and R⁴ are independently a hydrogen atom, R⁵ is atrifluoromethylsulfonyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is a bromine atom,R² and R³ are independently a hydrogen atom, R⁵ is atrifluoromethylsulfonyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R² is a methyl group,R³ and R⁴ are independently a hydrogen atom, R⁵ is atrifluoromethylsulfonyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a methyl group,R² and R⁴ are independently a hydrogen atom, R⁵ is atrifluoromethylsulfonyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is a methyl group,R² and R⁴ are independently a hydrogen atom, R⁵ is atrifluoromethylsulfonyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R² is atrifluoromethyl group, R³ and R⁴ are independently a hydrogen atom, R⁵is a trifluoromethylsulfonyl group, and R¹, A¹, A³ and n represent anyone of the combinations as listed in [Table 1] to [Table 35].

A compound, represented by the formula (A) wherein R³ is atrifluoromethyl group, R² and R⁴ are independently a hydrogen atom; R⁵is a trifluoromethylsulfonyl group, and R¹, A¹, A³ and n represent anyone of the combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is atrifluoromethyl group, R² and R³ are independently a hydrogen atom, R⁵is a trifluoromethylsulfonyl group, and R¹, A¹, A³ and n represent anyone of the combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is apentafluoroethyl group, R² and R⁴ are independently a hydrogen atom, R⁵is a trifluoromethylsulfonyl group, and R¹, A¹, A³ and n represent anyone of the combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is atrifluoromethoxy group, R² and R⁴ are independently a hydrogen atom, R⁵is a trifluoromethylsulfonyl group, and R¹, A¹, A³ and n represent anyone of the combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a 2-pyridylgroup, R² and R⁴ are independently a hydrogen atom, R⁵ is atrifluoromethylsulfonyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a3-chloro-2-pyridyl group, R² and R⁴ are independently a hydrogen atom,R⁵ is a trifluoromethylsulfonyl group, and R¹, A¹, A³ and n representany one of the combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a 2-pyrimidinylgroup, R² and R⁴ are independently a hydrogen atom, R⁵ is atrifluoromethylsulfonyl group, and R¹, A¹, A³ and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is —SF₅, R² and R⁴are independently a hydrogen atom, R⁵ is a trifluoromethylsulfonylgroup, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R², R³ and R⁴ areindependently a hydrogen atom, R⁵ is a bromine atom, and R¹, A¹, A³ andn represent any one of the combinations as listed in [Table 1] to [Table35].

A compound represented by the formula (A) wherein R² is a fluorine atom,R³ and R⁴ are independently a hydrogen atom, R⁵ is a bromine atom, andR¹, A¹, A³ and n represent any one of the combinations as listed in[Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a fluorine atom,R² and R⁴ are independently a hydrogen atom, R⁵ is a bromine atom, andR², A¹, A³ and n represent any one of the combinations as listed in[Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is a fluorine atom,R² and R³ are independently a hydrogen atom, R⁵ is a bromine atom, andR¹, A¹, A³ and n represent any one of the combinations as listed in[Table 1] to [Table 35].

A compound represented by the formula (A) wherein R² is a chlorine atom,R³ and R⁴ are independently a hydrogen atom, R⁵ is a bromine atom, andR¹, A¹, A³ and n represent any one of the combinations as listed in[Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a chlorine atom,R² and R⁴ are independently a hydrogen atom, R⁵ is a bromine atom, andR¹, A¹, A³ and n represent any one of the combinations as listed in[Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is a chlorine atom,R² and R³ are independently a hydrogen atom, R⁵ is a bromine atom, andR¹, A¹, A³ and n represent any one of the combinations as listed in[Table 1] to [Table 35].

A compound represented by the formula (A) wherein R² is a bromine atom,R³ and R⁴ are independently a hydrogen atom, R⁵ is a bromine atom, andR¹, A¹, A³ and n represent any one of the combinations as listed in[Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a bromine atom,R² and R⁴ are independently a hydrogen atom, R⁵ is a bromine atom, andR¹, A¹, A³ and n represent any one of the combinations as listed in[Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is a bromine atom,R² and R³ are independently a hydrogen atom, R⁵ is a bromine atom, andR¹, A¹, A³ and n represent any one of the combinations as listed in[Table 1] to [Table 35].

A compound represented by the formula (A) wherein R² is a methyl group,R³ and R⁴ are independently a hydrogen atom, R⁵ is a bromine atom, andR¹, A¹, A³ and n represent any one of the combinations as listed in[Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a methyl group,R² and R⁴ are independently a hydrogen atom, R⁵ is a bromine atom, andR¹, A¹, A³ and n represent any one of the combinations as listed in[Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is a methyl group,R² and R³ are independently a hydrogen atom, R⁵ is a bromine atom, andR¹, A¹, A³ and n represent any one of the combinations as listed in[Table 1] to [Table 35].

A compound represented by the formula (A) wherein R² is atrifluoromethyl group, R³ and R⁴ are independently a hydrogen atom, R⁵is a bromine atom, and R¹, A¹, A³ and n represent any one of thecombinations as listed in [Table 0.1] to [Table 35].

A compound represented by the formula (A) wherein R³ is atrifluoromethyl group, R² and R⁴ are independently a hydrogen atom, R⁵is a bromine atom, and R¹, A¹, A³ and n represent any one of thecombinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is atrifluoromethyl group, R² and R³ are independently a hydrogen atom, R⁵is a bromine atom, and R¹, A¹, A³ and n represent any one of thecombinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is apentafluoroethyl group, R² and R⁴ are independently a hydrogen atom, R⁵is a bromine atom, and R¹, A¹, A³ and n represent any one of thecombinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is atrifluoromethoxy group, R² and R⁴ are independently a hydrogen atom, R⁵is a bromine atom, and R¹, A¹, A³ and n represent any one of thecombinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a 2-pyridylgroup, R² and R⁴ are independently a hydrogen atom, R⁵ is a bromineatom, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a3-chloro-2-pyridyl group, R² and R⁴ are independently a hydrogen atom,R⁵ is a bromine atom, and R¹, A¹, A³ and n represent any one of thecombinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a 2-pyrimidinylgroup, R² and R⁴ are independently a hydrogen atom, R⁵ is a bromineatom, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is —SF₅, R² and R⁴are independently a hydrogen atom, R⁵ is a bromine atom, and R¹, A¹, A³and n represent any one of the combinations as listed in [Table 1] to[Table 35].

A compound represented by the formula (A) wherein R², R³ and R⁴ areindependently a hydrogen atom, R⁵ is a iodine atom, and R¹, A¹, A³ and nrepresent any one of the combinations as listed in [Table 1] to [Table35].

A compound represented by the formula (A) wherein R² is a fluorine atom,R³ and R⁴ are independently a hydrogen atom, R⁵ is a iodine atom, andR¹, A¹, A³ and n represent any one of the combinations as listed in[Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a fluorine atom,R² and R⁴ are independently a hydrogen atom, R⁵ is a iodine atom, andR¹, A¹, A³ and n represent any one of the combinations as listed in[Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is a fluorine atom,R² and R³ are independently a hydrogen atom, R⁵ is a iodine atom, andR¹, A¹, A³ and n represent any one of the combinations as listed in[Table 1] to [Table 35].

A compound represented by the formula (A) wherein R² is a chlorine atom,R³ and R⁴ are independently a hydrogen atom, R⁵ is a iodine atom, andR¹, A¹, A³ and n represent any one of the combinations as listed in[Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a chlorine atom,R² and R⁴ are independently a hydrogen atom, R⁵ is a iodine atom, andR¹, A¹, A³ and n represent any one of the combinations as listed in[Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is a chlorine atom,R² and R³ are independently a hydrogen atom, R⁵ is a iodine atom, andR¹, A¹, A³ and n represent any one of the combinations as listed in.[Table 1] to [Table 35].

A compound represented by the formula (A) wherein R² is a bromine atom,R³ and R⁴ are independently a hydrogen atom, R⁵ is a iodine atom, andR¹, A¹, A³ and n represent any one of the combinations as listed in[Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a bromine atom,R² and R⁴ are independently a hydrogen atom, R⁵ is a iodine atom, andR¹, A¹, A³ and n represent any one of the combinations as listed in[Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is a bromine atom,R² and R³ are independently a hydrogen atom, R⁵ is a iodine atom, andR¹, A¹, A³ and n represent any one of the combinations as listed in[Table 1] to [Table 35].

A compound represented by the formula (A) wherein R² is a methyl group,R³ and R⁴ are independently a hydrogen atom, R⁵ is a iodine atom, andR¹, A¹, A³ and n represent any one of the combinations as listed in[Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a methyl group,R² and R⁴ are independently a hydrogen atom, R⁵ is a iodine atom, andR¹, A¹, A³ and n represent any one of the combinations as listed in[Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is a methyl group,R² and R³ are independently a hydrogen atom, R⁵ is a iodine atom, andR¹, A¹, A³ and n represent any one of the combinations as listed in[Table 1] to [Table 35].

A compound represented by the formula (A) wherein R² is atrifluoromethyl group, R³ and R⁴ are independently a hydrogen atom, R⁵is a iodine atom, and R¹, A¹, A³ and n represent any one of thecombinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is atrifluoromethyl group, R² and R⁴ are independently a hydrogen atom, R⁵is a iodine atom, and R¹, A¹, A³ and n represent any one of thecombinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is atrifluoromethyl group, R² and R³ are independently a hydrogen atom, R⁵is a iodine atom, and R¹, A¹, A³ and n represent any one of thecombinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is apentafluoroethyl group, R² and R⁴ are independently a hydrogen atom, R⁵is a iodine atom, and R¹, A¹, A³ and n represent any one of thecombinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is atrifluoromethoxy group, R² and R⁴ are independently a hydrogen atom, R⁵is a iodine atom, and R¹, A¹, A³ and n represent any one of thecombinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a 2-pyridylgroup, R² and R⁴ are independently a hydrogen atom, R⁵ is a iodine atom,and R¹, A¹, A³ and n represent any one of the combinations as listed in[Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a3-chloro-2-pyridyl group, R² and R⁴ are independently a hydrogen atom,R⁵ is a iodine atom, and R¹, A¹, A³ and n represent any one of thecombinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a 2-pyrimidinylgroup, R² and R⁴ are independently a hydrogen atom, R⁵ is a iodine atom,and R¹, A¹, A³ and n represent any one of the combinations as listed in[Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is —SF₅, R² and R⁴are independently a hydrogen atom, R⁵ is a iodine atom, and R¹, A¹, A³and n represent any one of the combinations as listed in [Table 1] to[Table 35].

A compound represented by the formula (A) wherein R², R³ and R⁴ areindependently a hydrogen atom, R⁵ is —SF₅, and R¹, A¹, A³ and nrepresent any one of the combinations as listed in [Table 1] to [Table35].

A compound represented by the formula (A) wherein R² is a fluorine atom,R³ and R⁴ are independently a hydrogen atom, R⁵ is —SF₅, and R¹, A¹, A³and n represent any one of the combinations as listed in [Table 1] to[Table 35].

A compound represented by the formula (A) wherein R³ is a fluorine atom,R² and R⁴ are independently a hydrogen atom, R⁵ is —SF₅, and R¹, A¹, A³and n represent any one of the combinations as listed in [Table 1] to[Table 35].

A compound represented by the formula (A) wherein R⁴ is a fluorine atom,R² and R³ are independently a hydrogen atom, R⁵ is —SF₅, and R¹, A¹, A³and n represent any one of the combinations as listed in [Table 1] to[Table 35].

A compound represented by the formula (A) wherein R² is a chlorine atom,R³ and R⁴ are independently a hydrogen atom, R⁵ is —SF₅, and R¹, A¹, A³and n represent any one of the combinations as listed in [Table 1] to[Table 35].

A compound represented by the formula (A) wherein R³ is a chlorine atom,R² and R⁴ are independently a hydrogen atom, R⁵ is —SF₅, and R¹, A¹, A³and n represent any one of the combinations as listed in [Table 1] to[Table 35].

A compound represented by the formula (A) wherein R⁴ is a chlorine atom,R² and R³ are independently a hydrogen atom, R⁵ is —SF₅, and R¹, A¹, A³and n represent any one of the combinations as listed in [Table 1] to[Table 35].

A compound represented by the formula (A) wherein R² is a bromine atom,R³ and R⁴ are independently a hydrogen atom, R⁵ is —SF₅, and R¹, A¹, A³and n represent any one of the combinations as listed in [Table 1] to[Table 35].

A compound represented by the formula (A) wherein R³ is a bromine atom,R² and R⁴ are independently a hydrogen atom, R⁵ is —SF₅, and R¹, A¹, A³and n represent any one of the combinations as listed in. [Table 1] to[Table 35].

A compound represented by the formula (A) wherein R⁴ is a bromine atom,R² and R³ are independently a hydrogen atom, R⁵ is —SF₅, and R¹, A¹, A³and n represent any one of the combinations as listed in [Table 1] to[Table 35].

A compound represented by the formula (A) wherein R² is a methyl group,R³ and R⁴ are independently a hydrogen atom, R⁵ is —SF₅, and R¹, A¹, A³and n represent any one of the combinations as listed in [Table 1] to[Table 35].

A compound represented by the formula (A) wherein R³ is a methyl group,R² and R⁴ are independently a hydrogen atom, R⁵ is —SF₅, and R¹, A¹, A³and n represent any one of the combinations as listed in [Table 1] to[Table 35].

A compound represented by the formula (A) wherein R⁴ is a methyl group,R² and R³ are independently a hydrogen atom, R⁵ is —SF₅, and R¹, A¹, A³and n represent any one of the combinations as listed in [Table 1] to[Table 35].

A compound represented by the formula (A) wherein R² is atrifluoromethyl group, R³ and R⁴ are independently a hydrogen atom, R⁵is —SF₅, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is atrifluoromethyl group, R² and R⁴ are independently a hydrogen atom, R⁵is —SF₅, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R⁴ is atrifluoromethyl group, R² and R³ are independently a hydrogen atom, R⁵is —SF₅, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is apentafluoroethyl group, R² and R⁴ are independently a hydrogen atom, R⁵is —SF₅, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is atrifluoromethoxy group, R² and R⁴ are independently a hydrogen atom, R⁵is —SF₅, and R¹, A¹, A³ and n represent any one of the combinations aslisted in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a 2-pyridylgroup, R² and R⁴ are independently a hydrogen atom, R⁵ is —SF₅, and R¹,A¹, A³ and n represent any one of the combinations as listed in [Table1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a3-chloro-2-pyridyl group, R² and R⁴ are independently a hydrogen atom,R⁵ is —SF₅, and R¹, A¹, A³ and n represent any one of the combinationsas listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein R³ is a 2-pyrimidinylgroup, R² and R⁴ are independently a hydrogen atom, R⁵ is —SF₅, and R¹,A¹, A³ and n represent any one of the combinations as listed in [Table1] to [Table 35].

A compound represented by the formula (A) wherein R³ is —SF₅, R² and R⁴are independently a hydrogen atom, R⁵ is —SF₅, and R¹, A¹, A³ and nrepresent any one of the combinations as listed in [Table 1] to [Table35].

A compound represented by the formula (A) wherein A³ is ═N(→O)—, R², R³and R⁴ are independently a hydrogen atom, R⁵ is a trifluoromethyl group,and R¹, A¹, and n represent any one of the combinations as listed in[Table 1] to [Table 35].

A compound represented by the formula (A) wherein A is ═N(→O)—, R², R³and R⁴ are independently a hydrogen atom, R⁵ is a pentafluoroethylgroup, and R¹, A¹, and n represent any one of the combinations as listedin [Table 1] to [Table 35].

A compound represented by the formula (A) wherein A³ is ═N(→O)—, R², R³and R⁴ are independently a hydrogen atom, R⁵ is atrifluoromethylsulfonyl group, and R¹, A¹, and n represent any one ofthe combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein A³ is ═N(→O)—, R³ is atrifluoromethyl group, R² and R⁴ are independently a hydrogen atom, R⁵is a trifluoromethyl group, and R¹, A¹, and n represent any one of thecombinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein A³ is ═N(→O)—, R³ is atrifluoromethyl group, R² and R⁴ are independently a hydrogen atom, R⁵is a pentafluoroethyl group, and R¹, A¹, and n represent any one of thecombinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein A³ is ═N(→O)—, R³ is atrifluoromethyl group, R² and R⁴ are independently a hydrogen atom, R⁵is a trifluoromethylsulfonyl group, and R¹, A¹, and n represent any oneof the combinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein A³ is ═N(→O)—, R³ is apentafluoroethyl group, R² and R⁴ are independently a hydrogen atom, R⁵is a trifluoromethyl group, and R¹, A¹, and n represent any one of thecombinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein A³ is ═N(→O)—, R³ is apentafluoroethyl group, R² and R⁴ are independently a hydrogen atom, R⁵is a pentafluoroethyl group, and R¹, A¹, and n represent any one of thecombinations as listed in [Table 1] to [Table 35].

A compound represented by the formula (A) wherein A³ is ═N(→O)—, R³ is apentafluoroethyl group, R² and R⁴ are independently a hydrogen atom, R⁵is a trifluoromethylsulfonyl group, and R¹, A¹, and n represent any oneof the combinations as listed in [Table 1] to [Table 35].

Examples of pests on which the compound of the present inventionexhibits a controlling effect include arthropod pests such as harmfulinsects and harmful mites, and more specifically, the following pests.

Hemiptera:

Planthoppers (Delphacidae) such as small brown planthopper (Laodelphaxstriatellus), brown rice planthopper (Nilaparvata lugens), andwhite-backed rice planthopper (Sogatella furcifera); leafhoppers(Deltocephalidae) such as green rice leafhopper (Nephotettixcincticeps), green rice leafhopper (Nephotettix virescens), and teagreen leafhopper (Empoasca onukii); aphids (Aphididae) such as cottonaphid (Aphis gossypii), green peach aphid (Myzus persicae), cabbageaphid (Brevicoryne brassicae), piraea aphid (Aphis spiraecola), potatoaphid (Macrosiphum euphorbiae), foxglove aphid (Aulacorthum solani), oatbird-cherry aphid (Rhopalosiphum padi), tropical citrus aphid (Toxopteracitricidus), and mealy plum aphid (Hyalopterus pruni); stink bugs(Pentatomidae) such as green stink bug (Nezara antennata), bean bug(Riptortus clavetus), rice bug (Leptocorisa chinensis), white spottedspined bug (Eysarcoris parvus), and stink bug (Halyomorpha mista);whiteflies (Aleyrodidae) such as greenhouse whitefly (Trialeurodesvaporariorum), sweetpotato whitefly (Bemisia tabaci), silverleafwhitefly (Bemisia argentifolii), citrus whitefly (Dialeurodes citri),and citrus spiny white fly (Aleurocanthus spiniferus); scales (Coccidae)such as Calfornia red scale (Aonidiella aurantii), San Jose scale(Comstockaspis perniciosa), citrus north scale (Unaspis citri), red waxscale (Ceroplastes rubens), cottonycushion scale (Icerya purchasi),Japanese mealybug (Planococcus kraunhiae), Cosmstock mealybug(Pseudococcus longispinis), and white peach scale (Pseudaulacaspispentagona); lace bugs (Tingidae); cimices such as Cimex lectularius;psyllids (Psyllidae); etc.

Lepidoptera:

Pyralid moths (Pyralidae) such as rice stem borer (Chilo suppressalis),yellow rice borer (Tryporyza incertulas), rice leafroller(Cnaphalocrocis medinalis), cotton leafroller (Notarcha derogata),Indian meal moth (Plodia interpunctella), oriental corn borer (Ostriniafurnacalis), cabbage webworm (Hellula undalis), and bluegrass webworm(Pediasia teterrellus); owlet moths (Noctuidae) such as common cutworm(Spodoptera litura), beet armyworm (Spodoptera exigua), armyworm(Pseudaletia separata), cabbage armyworm (Mamestra brassicae), blackcutworm (Agrotis ipsilon), beet semi-looper (Plusia nigrisigna),Thoricoplusia spp., Heliothis spp., and Helicoverpa spp.; whitebutterflies (Pieridae) such as common white (Pieris rapae); tortricidmoths (Tortricidae) such as Adoxophyes spp., oriental fruit moth(Grapholita molesta), soybean pod borer (Leguminivora glycinivorella),azuki bean podworm (Matsumuraeses azukivora), summer fruit tortrix(Adoxophyes orana fasciata), smaller tea tortrix (Adoxophyes honmai.),oriental tea tortrix (Homona magnanima), apple tortrix (Archipsfuscocupreanus), and codling moth (Cydia pomonella); leafblotch miners(Graciilariidae) such as tea leafroller (Caloptilia theivora), and appleleafminer (Phyllonorycter ringoneella); Carposinidae such as peach fruitmoth (Carposina niponensis); lyonetiid moths (Lyonetiidae) such asLyonetia spp.; tussock moths (Lymantriidae) such as Lymantria spp., andEuproctis spp.; yponomeutid moths (Yponomeutidae) such as diamondback(Plutella xylostella); gelechiid moths (Gelechiidae) such as pinkbollworm (Pectinophora gossypiella), and potato tubeworm (Phthorimaeaoperculella); tiger moths and allies (Arctiidae) such as fall webworm(Hyphantria cunea); tineid moths (Tineidae) such as casemaking clothesmoth (Tinea translucens), and webbing clothes moth (Tineolabisselliella); etc.

Thysanoptera:

Thrips (Thripidae) such as yellow citrus thrips (Frankliniellaoccidentalis), melon thrips (Thrips palmi), yellow tea thrips(Scirtothrips dorsalis), onion thrips (Thrips tabaci), flower thrips(Frankliniella intonsa), etc.

Diptera:

Culices such as common mosquito (Culex pipiens pallens), Cluextritaeniorhynchus, and Cluex quinquefasciatus; Aedes spp. such as yellowfever mosquito (Aedes aegypti), and Asian tiger mosquito (Aedesalbopictus); Anopheles spp. such as Anopheles sinensis; chironomids(Chironomidae); house flies (Muscidae) such as Musca domestica, andMuscina stabulans; blow flies (Calliphoridae); flesh flies(Sarcophagidae); little house flies (Fanniidae); anthomyiid flies(Anthomyiidae) such as seedcorn fly (Delia platura), and onion fly(Delia antiqua); leafminer flies (Agromyzidae) such as rice leafminer(Agromyza oryzae), little rice leafminer (Hydrellia griseola), tomatoleafminer (Liriomyza sativae), legume leafminer (Liriomyza trifolii),and garden pea leafminer (Chromatomyia horticola); gout flies(Chloropidae) such as rice stem maggot (Chlorops oryzae); fruit flies(Tephritidae) such as melon fly (Dacus cucurbitae), and Meditteraneanfruit fly (Ceratitis capitata); Drosophilidae; humpbacked flies(Phoridae) such as Megaselia spiracularis; moth flies (Psychodidae) suchas Clogmia albipunctata; Simuliidae; Tabanidae such as horsefly (Tabanustrigonus); stable flies, etc.

Coleoptera:

Corn root worms (Diabrotica spp.) such as Western corn root worm(Diabrotica virgifera virgifera), and Sourthern corn root worm(Diabrotica undecimpunctata howardi); scarabs (Scarabaeidae) such ascupreous chafer (Anomala cuprea), soybean beetle (Anomala rufocuprea),and Japanese beetle (Popillia japonica); weevils such as maize weevil(Sitophilus zeamais), rice water weevil (Lissorhoptrus oryzophilus),azuki bean weevil (Callosobruchus chinensis), rice curculio(Echinocnemus squameus), boll weevil (Anthonomus grandis), and huntingbillbug (Sphenophorus venatus); darkling beetles (Tenebrionidae) such asyellow mealworm (Tenebrio molitor), and red flour beetle (Triboliumcastaneum); leaf beetles (Chrysomelidae) such as rice leaf beetle(Oulema oryzae), cucurbit leaf beetle (Aulacophora femoralis), stripedflea beetle (Phyllotreta striolata), and Colorado potato beetle(Leptinotarsa decemlineata); dermestid beetles (Dermestidae) such asvaried carper beetle (Anthrenus verbasci), and hide beetle (Dermestesmaculates); deathwatch beetles (Anobiidae) such as cigarette beetle(Lasioderma serricorne); Epilachna such as Twenty-eight-spotted ladybird(Epilachna vigintioctopunctata); bark beetles (Scolytidae) such aspowder-post beetle (Lyctus brunneus), and pine shoot beetle (Tomicuspiniperda); false powder-post beetles (Bostrychidae); spider beetles(Ptinidae); longhorn beetles (Cerambycidae) such as white-spottedlongicorn beetle (Anoplophora malasiaca); click beetles (Agriotes spp.);Paederus fuscipens, etc.

Orthoptera:

Asiatic locust (Locusta migratoria), African mole cricket (Gryllotalpaafricana), rice grasshopper (Oxya yezoensis), rice grasshopper (Oxyajaponica), Gryllidae, etc.

Shiphonaptera:

Cat flea (Ctenocephalides felis), dog flea (Ctenocephalides canis),human flea (Pulex irritans), oriental rat flea (Xenopsylla cheopis),etc.

Anoplura:

Human body louse (Pediculus humanus corporis), crab louse (Phthiruspubis), short-nosed cattle louse (Haematopinus eurysternus), sheep louse(Dalmalinia ovis), hog louse (Haematopinus suis), dog louse (Linognathussetosus), etc.

Damalinia:

Sheep body louse (Dalmalinia ovis), cattle biting louse (Dalmaliniabovis), chicken louse (Menopon gallinae), dog louse (Trichodectescanis), cat louse (Felicola subrostrata) etc.

Hymenoptera:

Ants (Formicidae) such as pharaoh ant (Monomorium pharaosis), negro ant(Formica fusca japonica), black house ant (Ochetellus glaber),Pristomyrmex pungens, Pheidole noda, leaf-cutting ant (Acromyrmex spp.),and fire ant (Solenopsis spp.); hornets (Vespidae); bethylid wasps(Betylidae); sawflies (Tenthredinidae) such as cabbage sawfly (Athaliarosae), and Athalia japonica, etc.

Nematoda:

Rice white-tip nematode (Aphelenchoides besseyi), strawberry budnematode (Nothotylenchus acris), southern root-knot nematode(Meloidogyne incognita), northern root-knot nematode (Meloidogynehapla), Javanese root-knot nematode (Meloidogyne javanica), soybean cystnematode (Heterodera glycines), potato cyst nematode (Globoderarostochiensis), coffee root-lesion nematode (Pratylenchus coffeae),California root-lesion nematode (Pratylenchus neglectus), etc.

Blattodea:

German cockroach (Blattella germanica), smokybrown cockroach(Periplaneta fuliginosa), American cockroach (Periplaneta americana),Periplaneta brunnea, oriental cockroach (Blatta orientalis);

Isoptera:

Termites such as Japanese subterranean termite (Reticulitermessperatus), Formosan subterranean termite (Coptotermes formosanus),western drywood termite (Incisitermes minor), Daikoku drywood termite(Cryptotermes domesticus), Odontotermes formosanus, Neotermeskoshunensis, Glyptotermes satsumesis, Giyptotermes nakajimai,Glyptotermes fuscus, Glyptotermes kodamai, Glyptotermes kushimensis,Japanese dampwood termite (Hodotermopsis japonica), Coptotermesguangzhoensis, Reticulitermes miyatakei, eastern subterranean termite(Reticulitermes flavipes amamianus), Reticulitermes sp., Nasutitermestakasagoesis, Pericapritermes nitobei, Sinocapritermes mushae,Reticuliterumes flavipes, Reticulitermes hesperus, Reticulitermesvirginicus, Reticulitermes tibialis, Heterotermes aureus, andZootermopsis nevadensis, etc.

Acarina:

Spider mites (Tetranychidae) such as two-spotted spider mite(Tetranychus urticae), Kanzawa spider mite (Tetranychus kanzawai),citrus red mite (Panonychus citri), European red mite (Panonychus ulmi),and Oligonychus spp.; eriophyid mites (Eriophyidae) such as pink citrusrust mite (Aculops pelekassi), Phyllocoptruta citri, tomato rust mite(Aculops lycopersici), purple tea mite (Calacarus carinatus), pink tearust mite (Acaphylla theavagran), Eriophyes chibaensis, and apple rustmite (Aculus schlechtendali); tarosonemid mites (Tarsonemidae) such asbroad mite (Polyphagotarsonemus latus); false spider mites(Tenuipalpidae) such as Brevipalpus phoenicis; Tuckerellidae; ticks(Ixodidae) such as Haemaphysalis longicornis, Haemaphysalis flava,Dermacentor taiwanicus, American dog tick (Dermacentor variabilis),Ixodes ovatus, Ixodes persulcatus, black leg tick (Ixodes scapularis),lone star tick (Amblyomma americanum), Boophilus microplus, andRhipicephalus sanguineus; Psoroptidae such as ear mite (Otodectescynotis); itch mites (Sarcoptidae) such as Sarcoptes scabiei; foliclemites (Demodicidae) such as dog folicle mite (Demodex canis); acaridmites (Acaridae) such as mold mite (Tyrophagus putrescentiae), andTyrophagus similis; house dust mites (Pyroglyphidae) such asDermatophagoides farinae, and Dermatophagoides ptrenyssnus; cheyletidemites (Cheyletidae) such as Cheyletus eruditus, Cheyletus malaccensis,and Cheyletus moorei; parasitoid mites (Dermanyssidae) such as tropicalrat mite (Ornithonyssus bacoti), northern fowl mite (Ornithonyssussylviarum), and poultry red mite (Dermanyssus gallinae); chiggers(Trombiculidae) such as Leptotrombidium akamushi; spiders (Araneae) suchas Japanese foliage spider (Chiracanthium japonicum), redback spider(Latrodectus hasseltii), etc.

Chilopoda: house centipede (Thereuonema hilgendorfi), Scolopendrasubspinipes, etc.;

Diplopoda: garden millipede (Oxidus gracilis), Nedyopus tambanus, etc.;

Isopoda: common pill bug (Armadillidium vulgare), etc.;

Gastropoda: Limax marginatus, Limax flavus, etc.

The pest control agent of the present invention comprises the presentcompound and an inert carrier. The pest control agent of the presentinvention generally comprises the present compound in combination with asolid carrier, a liquid carrier and/or a gaseous carrier, and ifnecessary, a surfactant or other formulation additives and takes theform of emulsifiable concentrate, oil solution, dusts, granules,wettable powder, suspension concentrate, microcapsules, aerosol, smokingagent, poison bait, resin formulation, shampoo formulation, paste, foam,carbon dioxide gas formulation, tablet or the like. The pesticidalcomposition of the present invention may be processed into mosquitocoil, electric mosquito mat, electric mosquito liquid, smoking agent,fumigant, sheet, spot-on pesticide, or oral pesticide, and then be used.

The pesticidal composition of the present invention generally contains0.01 to 95% by weight of the compound of the present invention.

Examples of the solid carrier to be used for formulation include a finepower and a granule of clays (e.g., kaolin clay, diatomite, bentonite,Fubasami clay, and acid clay), synthetic hydrated silicon oxide, talc,ceramic, other inorganic minerals (e.g., sericite, quartz, sulfur,activated carbon, calcium carbonate, and hydrated silica), and chemicalfertilizers (e.g., ammonium sulfate, ammonium phosphate, ammoniumnitrate, urea, and ammonium chloride) as well as synthetic resins (e.g.,polypropylene, polyacrylonitrile, polyester resins such as methylpolymethacrylate and polyethylene terephthalate, nylon resins such asnylon-6, nylon-11, and nylon-66, polyamide resins, polyvinyl chloride,polyvinylidene chloride, and vinyl chloride-propylene copolymer).

Examples of the liquid carrier include water, alcohols (e.g., methanol,ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethyleneglycol, propylene glycol, and phenoxyethanol), ketones (e.g., acetone,methyl ethyl ketone, and cyclohexanone), aromatic hydrocarbons (e.g.,toluene, xylene, ethylbenzene, dodecylbenzene, phenylxylylethane, andmethylnaphthalene), aliphatic hydrocarbons (e.g., hexane, cyclohexane,kerosine, and light oil), esters (e.g., ethyl acetate, butyl acetate,isopropyl mylistate, ethyl oleate, diisopropyl adipate, diisobutyladipate, and propyleneglycol monomethyl ether acetate), nitriles (e.g.,acetonitrile and isobutyronitrile), ethers (e.g., diisopropyl ether,1,4-dioxane, ethylene glycol dimethyl ether, diethylene glycol dimethylether, diethylene glycol monomethyl ether, propylene glycol monomethylether, dipropylene glycol monomethyl ether, and3-methoxy-3-methyl-1-butanol), acid amides (e.g., N,N-dimethylformamideand N,N-dimethylacetamide), halogenated hydrocarbons (e.g.,dichloromethane, trichloroethane, and tetrachlorocarbon), sulfoxides(e.g., dimethylsulfoxide), propylene carbonate, and vegetable oils(e.g., soy bean oil and cotton seed oil).

Examples of the gaseous carrier include fluorocarbons, butane gas,liquefied petroleum gas (LPG), dimethyl ether, and carbon dioxide.

Examples of the surfactant include nonionic surfactant such aspolyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, andpolyethyleneglycol fatty acid ester; and anionic surfactant such asalkylsulfonic acid salts, alkylbenzenesulfonic acid salts, andalkylsulfuric acid salts.

Examples of the other formulation additives include binders,dispersants, colorants and stabilizers, and particularly for example,casein, gelatin, polysaccharides (e.g., starch, gum arabic, cellulosederivatives, and alginic acid), lignin derivatives, syntheticwater-soluble polymers (e.g., polyvinyl alcohol, polyvinylpyrrolidone,and polyacrylic acid), PAP (acidic isopropyl phosphate), BHT(2,6-di-t-butyl-4-methylphenol), and BHA (a mixture of2-t-butyl-4-methoxyphenol and 3-t-butyl-4-methoxyphenol).

Examples of a base material for the resin formulation include vinylchloride polymers, and polyurethane. To the base material, if necessary,a plasticizer such as phthalate (e.g., dimethyl phthalate, dioctylphthalate, etc.), adipate, stearic acid or the like may be added. Theresin formulation is prepared by kneading the compound of the presentinvention into the base material using a conventional kneader, followedby molding such as injection molding, extrusion molding, press moldingor the like. The resulting resin formulation may be formed into theshape of a plate, a film, a tape, a net, a string or the like via afurther step of molding, cutting, or the like, if necessary. These resinformulations may be used, for example, the form of an animal collar, ananimal ear tag, a sheet, a lead, or a horticultural post.

Examples of a base material of the poison bait include cereal powder,vegetable oil, sugar, and crystalline cellulose. To the base material,if necessary, an antioxidant such as dibutylhydroxytoluene, ornordihydroguaiaretic acid, a preservative such as dehydroacetic acid, anagent for preventing children or pets from erroneously eating such ashot pepper powder, a pest-attractive perfume such as cheese perfume,onion perfume- or peanut oil or the like may be added.

The method for controlling a pest of the present invention is applyingan effective amount of the present compound to a pest directly and/or ahabitat of a pest (e.g., plant, soil, indoor, and in-body of animals).The present compound is generally used as the pest control agent of thepresent invention in the method for controlling pests of the presentinvention.

When the pest control agent of the present invention is used for acontrol of pests in agriculture, the application amount is usually 1 to10,000 g as the present compound per 10,000 m². When the pest controlagent of the present invention is a formulation of emulsion, wettablepowder or flowable, it is generally applied after a dilution with waterto have an active ingredient concentration of 0.01 to 10,000 ppm. Whenthe pest control agent of the present invention is a formulation ofgranules or dusts, they are generally applied as such.

The formulations and the dilute aqueous solutions of the formulation maybe sprayed directly to the plant to be protected from pests, or may beapplied to the soil to control the pests living in a soil.

Furthermore, the resin formulation of sheet or strip form can be appliedby a method such as winding around plants, stretching in the vicinity ofplants, and laying on the soil surface at the plant bottom.

When the pest control agent of the present invention is used for acontrol of pests in indoor, the application amount is usually 0.01 to1,000 mg as the present compound per 1 m² in case of application forplane surface, and 0.01 to 500 mg as the present compound per 1 m³ incase of application for space. When the pest control agent of thepresent invention is a formulation of emulsions, wettable powders orflowables, they are usually applied after a dilution with water to havean active ingredient concentration of 0.1 to 1,000 ppm. When the pestcontrol agent of the present invention is a formulation of oilsolutions, aerosols, smoking agents and poison baits, they are usuallyapplied as such.

When the pesticidal composition of the present invention is used forcontrolling external parasites of livestock such as a cow, a horse, apig, a sheep, a goat and a chicken, or small animals such as a dog, acat, a rat and a mouse, it can be applied to said animals by a knownmethod in the veterinary field. Specifically, when systemic control isintended, the pesticidal composition of the present invention isadministered, for example, as a tablet, a mixture with feed, asuppository or an injection (e.g., intramuscularly, subcutaneously,intravenously, intraperitoneally, etc.). When non-systemic control isintended, a method of using the pesticidal composition of the presentinvention includes spraying, pour-on treatment or a spot-on treatmentwith the pesticidal composition in the form of an oil solution or anaqueous liquid, washing an animal with the pesticidal composition in theform of a shampoo formulation, and attachment of a collar or a ear tagmade of the pesticidal composition in the form of a resin formulation toan animal. When administered to an animal, the amount of the compound ofthe present invention is usually in the range of 0.1 to 1,000 mg per 1kg body weight of the animal.

The pest control agent of the present invention could be used infarmlands on which “crops” shown below are cultivated.

Agricultural crops: corn, rice, wheat, barley, rye, oat, sorghum,cotton, soybean, peanut, sarrazin, sugar beet, rapeseed, sunflower,sugar cane, and tobacco;

Vegetables: Solanaceae vegetables (e.g., eggplant, tomato, green pepper,hot pepper, and potato), Cucurbitaceae vegetables (e.g., cucumber,pumpkin, zucchini, watermelon, and melon), Cruciferae vegetables (e.g.,Japanese radish, turnip, horseradish, kohlrabi, Chinese cabbage,cabbage, brown mustard, broccoli, and cauliflower), Compositaevegetables (e.g., burdock, garland chrysanthemum, artichoke, andlettuce), Liliaceae vegetables (e.g., Welsh onion, onion, garlic, andasparagus), Umbelliferae vegetables (e.g., carrot, parsley, celery, andparsnip), Chenopodiaceae vegetables (e.g., spinach, and Swiss chard),Labiatae vegetables (e.g., Japanese basil, mint, and basil), strawberry,sweat potato, yam, and aroid;

Fruit trees: pomaceous fruits (e.g., apple, common pear, Japanese pear,Chinese quince, and quince), stone fleshy fruits (e.g., peach, plum,nectarine, Japanese plum, cherry, apricot, and prune), citrus plants(e.g., Satsuma mandarin, orange, lemon, lime, and grapefruit), nuts(e.g., chestnut, walnut, hazel nut, almond, pistachio, cashew nut, andmacadamia nut), berry fruits (e.g., blueberry, cranberry, blackberry,and raspberry), grape, persimmon, olive, loquat, banana, coffee, date,coconut palm, and oil palm;

Trees other fruit trees: tea, mulberry, flowering trees (e.g., azalea,japonica, hydrangea, sasanqua, lllicium anisatum, cherry tree, tulippoplar, crepe myetle, and orange osmanthus), street trees (e.g., ashtree, birch, dogwood, eucalyptus, ginkgo, lilac, maple tree, oak,poplar, cercis, Chinese sweet gum, plane tree, zelkova, Japanesearborvitae, fir tree, Japanese hemlock, needle juniper, pine, spruce,yew, elm, and horse-chestnut), sweet viburnum, Podocarpus macrophyllus,Japanese cedar, Japanese cypress, croton, spindle tree, and Chainesehowthorn.

Lawn: zoysia (e.g., Japanese lawn grass and mascarene grass), Bermudagrass (e.g., Cynodon dactylon), bent grass (e.g., creeping bent grass,Agrostis stolonifera, and Agrostis tenuis), bluegrass (e.g., Kentuckybluegrass and rough bluegrass), fescue (e.g., tall fescue, chewingfescue, and creeping fescue), ryegrass (e.g., darnel and perennialryegrass), cocksfoot, and timothy grass;

Others: flowers (e.g., rose, carnation, chrysanthemum, Eustomagrandiflorum Shinners, gypsophila, gerbera, pot marigold, salvia,petunia, verbena, tulip, aster, gentian, lily, pansy, cyclamen, orchid,lily of the valley, lavender, stock, ornamental kale, primula,poinsttia, gladiolus, cattleya, daisy, cymbidium, and begonia), biofuelplants (e.g., Jatropha, curcas, safflower, Camelina alyssum,switchgrass, miscanthus, reed canary grass, Arundo donax, kenaf,cassava, willow, and algae), and foliage plant.

The “crops” include genetically modified crops.

The pest control agent of the present invention can be used as a mixturewith or together with other insecticides, acaricides, nematocides,fungicides, plant growth regulators, herbicides, and synergists.Examples of active ingredients of the insecticide, the acaricide, thenematocide, the fungicide, the herbicide, and the synergist are shownbelow.

Examples of active ingredients of the insecticides include:

(1) organic phosphorus compounds:

acephate, aluminium phosphide, butathiofos, cadusafos, chlorethoxyfos,chlorfenvinphos, chlorpyrifos, chlorpyrifos-methyl, cyanophos: CYAP,diazinon, DCIP (dichlorodiisopropyl ether), dichlofenthion: ECP,dichlorvos: DDVP, dimethoate, dimethylvinphos, disulfoton, EPN, ethion,ethoprophos, etrimfos, fenthion: MPP, fenitrothion: MEP, fosthiazate,formothion, Hydrogen phosphide, isofenphos, isoxathion, malathion,mesulfenfos, methidathion: DMTP, monocrotophos, naled: BRP, oxydeprofos:ESP, parathion, phosalone, phosmet: PMP, pirimiphos-methyl,pyridafenthion, quinalphos, phenthoate: PAP, profenofos, propaphos,prothiofos, pyraclorfos, salithion, sulprofos, tebupirimfos, temephos,tetrachlorvinphos, terbufos, thiometon, trichlorphon: DEP, vamidothion,phorate, and cadusafos.

(2) carbamate compounds:

alanycarb, bendiocarb, benfuracarb, BPMC, carbaryl, carbofuran,carbosulfan, cloethocarb, ethiofencarb, fenobucarb, fenothiocarb,fenoxycarb, furathiocarb, isoprocarb: MIPC, metolcarb, methomyl,methiocarb, NAC, oxamyl, pirimicarb, propoxur: PHC, XMC, thiodicarb,xylylcarb, and aldicarb.

(3) synthetic pyrethroid compounds:

acrinathrin, allethrin, benfluthrin, beta-cyfluthrin, bifenthrin,cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin, deltamethrin,esfenvalerate, ethofenprox, fenpropathrin, fenvalerate, flucythrinate,flufenoprox, flumethrin, fluvalinate, halfenprox, imiprothrin,permethrin, prallethrin, pyrethrins, resmethrin, sigma-cypermethrin,silafluofen, tefluthrin, tralomethrin, transfluthrin, tetramethrin,phenothrin, cyphenothrin, alpha-cypermethrin, zeta-cypermethrin,lambda-cyhalothrin, gamma-cyhalothrin, furamethrin, tau-fluvalinate,metofluthrin, profluthrin, dimefluthrin, 2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl(EZ)-(1RS,3RS;1RS,3SR)-2,2-dimethyl-3-prop-1-enylcyclopropanecarboxylate,2,3,5,6-tetrafluoro-4-methylbenzyl(EZ)-(1RS,3RS;1RS,3SR)-2,2-dimethyl-3-prop-1-enylcyclopropanecarboxylate, and2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl(1RS,3RS;1RS,3SR)-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate,2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl(EZ)-(1RS,3RS;1RS,3SR)-2,2-dimethyl-3-(2-cyano-1-propenyl)cyclopropanecarboxylate.

(4) nereistoxin compounds:

cartap, bensultap, thiocyclam, monosultap, and bisultap.

(5) neonicotinoid compounds:

imidacloprid, nitenpyram, acetamiprid, thiamethoxam, thiacloprid,dinotefuran, and clothianidin.

(6) benzoylurea compounds:

chlorfluazuron, bistrifluron, diafenthiuron, diflubenzuron, fluazuron,flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron,noviflumuron, teflubenzuron, triflumuron, and triazuron.

(7) phenylpyrazole compounds:

acetoprole, ethiprole, fipronil, vaniliprole, pyriprole, andpyrafluprole.

(8) Bt toxin insecticides:

live spores derived from and crystal toxins produced from Bacillusthuringiesis and a mixture thereof;

(9) hydrazine compounds:

chromafenozide, halofenozide, methoxyfenozide, and tebufenozide.

(10) organic chlorine compounds:

aldrin, dieldrin, dienochlor, endosulfan, and methoxychlor.

(11) other insecticides:

machine oil, nicotine-sulfate; avermectin-B, bromopropylate, buprofezin,chlorphenapyr, cyantraniliprole, cyromazine, D-D (1,3-Dichloropropene),emamectin-benzoate, fenazaquin, flupyrazofos, hydroprene, methoprene,indoxacarb, metoxadiazone, milbemycin-A, pymetrozine, pyridalyl,pyriproxyfen, spinosad, sulfluramid, tolfenpyrad, triazamate,flubendiamide, lepimectin, Arsenic acid, benclothiaz, Calcium cyanamide,Calcium polysulfide, chlordane, DDT, DSP, flufenerim, flonicamid,flurimfen, formetanate, metam-ammonium, metam-sodium, Methyl bromide,Potassium oleate, protrifenbute, spiromesifen, sulfoxaflor, Sulfur,metaflumizone, spirotetramat, pyrifluquinazone, spinetoram,chlorantraniliprole, tralopyril, cyantraniliprole, a compoundrepresented by the following formula (K):

whereinR¹⁰⁰ represents chlorine, bromine or a trifluoromethyl group,R²⁰⁰ represents chlorine, bromine or a methy group,R³⁰⁰ represents chlorine, bromine or a cyano group, and

A compound represented by the following formula (L):

whereinR¹⁰⁰⁰ represents chlorine, bromine or iodine.

Examples of active ingredients of the acaricides include acequinocyl,amitraz, benzoximate, bifenaate, bromopropylate, chinomethionat,chlorobenzilate, CPCBS (chlorfenson), clofentezine, cyflumetofen,dicofol, etoxazole, fenbutatin oxide, fenothiocarb, fenpyroximate,fluacrypyrim, fluproxyfen, hexythiazox, propargite: BPPS, polynactins,pyridaben, Pyrimidifen, tebufonpyrad, tetradifon, spirodiclofen,spiromesifen, spirotetramat, amidoflumet, and cyenopyrafen.

Examples of active ingredients of the nematicides include DCIP,fosthiazate, levamisol, methyisothiocyanate, morantel tartarate, andimicyafos.

Examples of active ingredients of the fungicides include azolefungicidal compounds such as propiconazole, prothioconazole,triadimenol, prochloraz, penconazole, tebuconazole, flusilazole,diniconazole, bromuconazole, epoxiconazole, difenoconazole,cyproconazole, metconazole, triflumizole, tetraconazole, myclobutanil,fenbuconazole, hexaconazole, fluquinconazole, triticonazole, bitertanol,imazalil, and flutriafol;

cyclic amine fungicidal compouds such as fenpropimorph, tridemorph, andfenpropidin;benzimidazole fungicidal compounds such as carbendezim, benomyl,thiabendazole, and thiophanate-methyl;procymidone; cyprodinil; pyrimethanil; diethofencarb; thiuram;fluazinam; mancozeb; iprodione; vinclozolin; chlorothalonil; captan;mepanipyrim; fenpiclonil; fludioxonil; dichlofluanid; folpet;kresoxim-methyl; azoxystrobin; trifloxystrobin; fluoxastrobin;picoxystrobin; pyraclostrobin; dimoxystrobin; pyribencarb; spiroxamine;quinoxyfen; fenhexamid; famoxadone; fenamidone; zoxamide; ethaboxam;amisulbrom; iprovalicarb; benthiavalicarb; cyazofamid; mandipropamid;boscalid; penthiopyrad; metrafenone; fluopiran; bixafen; cyflufenamid;proquinazid; isotianil and tiadinil.

Examples of active ingredients of the herbicides and the phytohormoneagents include:

(1) phenoxyfatty acid herbicidal compounds such as 2,4-PA, MCP, MCPB,phenothiol, mecoprop, fluroxypyr, triclopyr, clomeprop, andnaproanilide.(2) benzoic acid herbicidal compounds such as 2,3,6-TBA, dicamba,clopyralid, picloram, aminopyralid, quinclorac, and quinmerac.(3) urea herbicidal compounds such as diuron, linuron, chlortoluron,isoproturon, fluometuron, isouron, tebuthiuron, methabenzthiazuron,cumyluron, daimuron, and methyl-daimuron.(4) triazine herbicidal compounds such as atrazine, ametoryn, cyanazine,simazine, propazine, simetryn, dimethametryn, prometryn, metribuzin,triaziflam, and indaziflam.(5) bipyridinium herbicidal compounds such as paraquat, and diquat.(6) hydroxybenzonitrile herbicidal compounds such as bromoxynil, andioxynil.(7) dinitroaniline herbicidal compounds such as pendimethalin,prodiamine, and trifluralin.(8) organic phosphorus herbicidal compounds such as amiprofos-methyl,butamifos, bensulide, piperophos, anilofos, glyphosate, glufosinate,glufosinate-P, and bialaphos.(9) carbamate herbicidal compounds such as di-allate, tri-allate, EPTC,butylate, benthiocarb, esprocarb, molinate, dimepiperate, swep,chlorpropham, phenmedipham, phenisopham, pyributicarb, and asulam.(10) acid amide herbicidal compounds such as propanil, propyzamide,bromobutide) and etobenzanid.(11) chloroacetanilide herbicidal compounds such as acetochlor,alachlor, butachlor, dimethenamid, propachlor, metazachlor, metolachlor,pretilachlor, thenylchlor, and pethoxamid.(12) diphenylether herbicidal compounds such as acifluorfen-sodium,bifenox, oxyfluorfen, lactofen), fomesafen, chlomethoxynil, andaclonifen.(13) cyclic imide herbicidal compounds such as oxadiazon, cinidon-ethyl,carfentrazone-ethyl, surfentrazone, flumiclorac-pentyl, flumioxazin,pyraflufen-ethyl, oxadiargyl, pentoxazone, fluthiacet-methyl,butafenacil, benzfendizone, bencarbazone, and saflufenacil.(14) pyrazole herbicidal compounds such as benzofenap, pyrazolate,pyrazoxyfen, topramezone, and pyrasulfotole.(15) triketone herbicidal compounds such as isoxaflutole, benzobicyclon,sulcotrione, mesotrione, tembotrione, and tefuryltrione.(16) aryloxyphenoxypropionic acid herbicidal compounds such asclodinafop-propargyl, cyhalofop-butyl, diclofop-methyl,fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl, andquizalofop-ethyl, metamifop.(17) trioneoxime herbicidal compounds such as alloxydim-sodium,sethoxydim, butroxydim, clethodim, cloproxydim, cycloxydim,tepraloxydim, tralkoxydim, and profoxydim.(18) sulfonylurea herbicidal compounds such as chlorsulfuron,sulfometuron-methyl, metsulfuron-methyl, chlorimuron-ethyl,tribenuron-methyl, triasulfuron, bensulfuron-methyl,thifensulfuron-methyl, pyrazosulfuron-ethyl, primisulfuron-methyl,nicosulfuron, amidosulfuron, cinosulfuron, imazosulfuron, rimsulfuron,halosulfuron-methyl, prosulfuron, ethametsulfuron-methyl,triflusulfuron-methyl, flazasulfuron, cyclosulfamuron, flupyrsulfuron,sulfosulfuron, azimsulfuron, ethoxysulfuron, oxasulfuron,iodosulfuron-methyl-sodium, foramsulfuron, mesosulfuron-methyl,trifloxysulfuron, tritosulfuron, orthosulfamuron, flucetosulfuron, andpropyrisulfuron.(19) imidazolinone herbicidal compounds such as imazamethabenz-methyl,imazamethapyr, imazamox, imazapyr, imazaquin, and imazethapyr.(20) sulfonamide herbicidal compounds such as flumetsulam, metosulam,diclosulam, florasulam, cloransulam-methyl, penoxsulam, and pyroxsulam.(21) pyrimidinyloxybenzoic acid herbicidal compounds such aspyrithiobac-sodium, bispyribac-sodium, pyriminobac-methyl, pyribenzoxim,pyriftalid, and pyrimisulfan.(22) other herbicidal compounds such as bentazon, bromacil, terbacil,chlorthiamid, isoxaben, dinoseb, amitrole, cinmethylin, tridiphane,dalapon, diflufenzopyr-sodium, dithiopyr, thiazopyr,flucarbazone-sodium, propoxycarbazone-sodium, mefenacet, flufenacet,fentrazamide, cafenstrole, indanofan, oxaziclomefone, benfuresate, ACN,pyridate, chloridazon, norflurazon, flurtamone, diflufenican,picolinafen, beflubutamid, clomazone, amicarbazone, pinoxaden,pyraclonil, pyroxasulfone, thiencarbazone-methyl, aminocyclopyrachlor,ipfencarbazone, and methiozolin.

Examples of active ingredients of the synergists include piperonylbutoxide, sesamex, sulfoxide,N-(2-ethylhexyl)-8,9,10-trinorborn-5-ene-2,3-dicarboximide (MGK 264),N-declyimidazole, WARF-antiresistant, TBPT, TPP, IBP, PSCP, methyliodide (CH₃I), t-phenylbutenone, diethylmaleate, DMC, FDMC, ETP, andETN.

EXAMPLES

Hereinafter, the present invention is described in more detail byreference to Production Examples, Reference Production Examples,Formulation Examples and Test Examples which the present invention isnot limited to.

Firstly, Production Examples of the present compound are describedbelow.

Production Example 1 (1)

A mixture of N²-methyl-5-trifluoromethylpyridin-2,3-diamine (0.76 g),3-fluoropyridin-2-carboaldehyde (0.50 g), sodium hydrogen sulfite (0.50g) and DMF (3 ml) was stirred at 120° C. for 8 hours. To the cooledreaction mixture was added saturated aqueous sodium hydrogen carbonatesolution, and extracted with ethyl acetate. The organic layer was washedwith water, dried over anhydrous magnesium sulfate, and concentratedunder reduced pressure. The residue was subjected to silica gel columnchromatography to give2-(3-fluoropyridin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine(0.43 g), which is hereinafter referred to as “intermediate compound(M6-2)”.

Intermediate Compound (M6-2)

¹H-NMR (CDCl₃) δ: 8.75 (1H, d), 8.66-8.63 (1H, m), 8.40 (1H, d),7.73-7.67 (1H, m), 7.56-7.51 (1H, m), 4.16 (3H, s).

Production Example 1 (2)

To a mixture of the intermediate compound (M6-2) (1.23 g) and DMF (3.5ml) was added sodium ethanethiolate (0.48 g) while ice-cooling, and themixture was stirred at room temperature for 2 hours. To the reactionmixture was added water, and the mixture was extracted with ethylacetate. The organic layer was washed with water, dried over anhydrousmagnesium sulfate, and concentrated under reduced pressure. Theresulting residue was subjected to silica gel column chromatography togive 2-(3-ethylsulfanylpyridin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (1.39g), which is hereinafter referred to as “the present compound 1”.

The Present Compound 1

¹H-NMR (CDCl₃) δ: 8.73 (1H, d), 8.53 (1H, dd), 8.39 (1H, d), 7.80 (1H,dd), 7.40 (1H, dd), 4.04 (3H, s), 2.97 (2H, q), 1.35 (3H, t).

Production Examples 2 and 3

To a mixture of 2-(3-ethylsulfanylpyridin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (0.62g) and chloroform (10 ml) was added m-chloroperbenzoic acid (purity: notless than 65%) (0.79 g) while ice-cooling, and then the mixture wasstirred at room temperature for 5 hours. To the reaction mixture waspoured saturated aqueous sodium hydrogen carbonate solution, and themixture was extracted with chloroform. The organic layer was washed withwater, dried over anhydrous magnesium sulfate, and concentrated underreduced pressure. The resulting residue was subjected to silica gelcolumn chromatography to give 2-(3-ethylsulfinylpyridin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (87mg), which is hereinafter referred to as “the present compound 2”, and2-(3-ethylsulfonylpyridin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine(0.49 g), which is hereinafter referred to as “the present compound 3”.

The Present Compound 2

¹H-NMR (CDCl₃) δ: 8.85 (1H, dd), 8.77 (1H, s), 8.67 (1H, dd), 8.34 (1H,s), 7.69 (1H, dd), 4.36 (3H, s), 3.72-3.62 (1H, m), 3.14-3.04 (1H, m),1.47 (3H, t).

The Present Compound 3

¹H-NMR (CDCl₃) δ: 9.01 (1H, dd), 8.76 (1H, s), 8.55 (1H, dd), 8.31 (1H,s), 7.74 (1H, dd), 3.88 (3H, s), 3.83 (2H, q), 1.37 (3H, t).

Production Example 4 (1)

A mixture of N²-methyl-5-trifluoromethylpyridin-2,3-diamine (0.70 g),3-chloro-5-trifluoromethylpyridin-2-carboxylic acid (0.53 g), WSC (0.82g), HOBt (42 mg) and pyridine (4.5 ml) was stirred at 60° C. for 4hours. To the cooled reaction mixture was added water, and the mixturewas extracted with ethyl acetate. The organic layer was washed withwater, dried over anhydrous magnesium sulfate, and concentrated underreduced pressure to give an intermediate compound (M20-3).

Intermediate Compound (M20-3)

A mixture of the resulting intermediate compound (M3-4) (total amount),p-toluenesulfonic acid monohydrate (1.04 g) and N-methylpyrrolidinone (4ml) was stirred while heating to 150° C. for 2.5 hours. To the cooledreaction mixture was added saturated aqueous sodium hydrogen carbonatesolution, and the mixture was extracted with ethyl acetate. The organiclayer was washed with water, dried over anhydrous magnesium sulfate, andconcentrated under reduced pressure. The resulting residue was subjectedto silica gel column chromatography to give2-(3-chloro-5-trifluoromethylpyridin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine(0.71 g), which is hereinafter referred to as “intermediate compound(M6-3)”.

Intermediate Compound (M6-3)

¹H-NMR (CDCl₃) δ: 8.96 (1H, d), 8.79 (1H, d), 8.42 (1H, d), 8.22 (1H,d), 4.02 (3H, s).

Production Example 4 (2)

To a mixture of2-(3-chloro-5-trifluoromethylpyridin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine(0.71 g) and DMF (4 ml) was added sodium ethanethiolate (0.24 g) whileice-cooling, and the mixture was stirred at room temperature for 1 hour.To the reaction mixture was added water, and the mixture was extractedwith ethyl acetate. The organic layer was washed with water, dried overanhydrous magnesium sulfate, and concentrated under reduced pressure togive2-(3-ethylsulfanyl-5-trifluoromethylpyridin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine(0.76 g), which is hereinafter referred to as “the present compound 4”.

The Present Compound 4

¹H-NMR (CDCl₃) δ: 8.77 (1H, d), 8.75 (1H, d), 8.43 (1H, d), 7.93 (1H,d), 4.11 (3H, s), 3.02 (2H, q), 1.40 (3H, t).

Production Example 5

To a mixture of2-(3-ethylsulfanyl-5-trifluoromethylpyridin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine(0.61 g) and chloroform (10 ml) was added m-chloroperbenzoic acid(purity: not less than 65%) (0.66 g) while ice-cooling, and the mixturewas stirred at room temperature for 10 hours. To the reaction mixturewere added aqueous 10% sodium thiosulfate solution and saturated aqueoussodium hydrogen carbonate solution, and the mixture was extracted withchloroform. The organic layer was washed with water, dried overanhydrous magnesium sulfate, and concentrated under reduced pressure togive2-(3-ethylsulfonyl-5-trifluoromethylpyridin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine(0.62 g), which is hereinafter referred to as “the present compound 5”.

The Present Compound 5

¹H-NMR (CDCl₃) δ: 9.25 (1H, d), 8.80 (1H, d), 8.79 (1H, d), 8.34 (1H,d), 3.96 (2H, q), 3.94 (3H, s), 1.42 (3H, t).

Production Example 6

A mixture of2-(3-ethylsulfanyl-pyridin-2-yl)-6-iodo-3-methyl-3H-imidazo[4,5-b]pyridine(835 mg), sodium pentafluoropropionate (2.0 g), copper iodide (2.0 g),NMP (10 ml) and xylene (50 ml) was stirred while heating to 150° C. for8 hours. After allowing to cool to room temperature, to the reactionmixture were added 40% aqueous ammonia solution and saturated aqueoussodium hydrogen carbonate solution and the mixture was extracted withethyl acetate. The organic layer was dried over sodium sulfate, andconcentrated under reduced pressure. The residue was subjected to silicagel column chromatography to give2-(3-ethylsulfanyl-pyridin-2-yl)-3-methyl-6-pentafluoroethyl-3H-imidazo[4,5-b]pyridine(303 mg), which is hereinafter referred to as “the present compound 6”.

The Present Compound 6

¹H-NMR (CDCl₃) δ: 8.69 (1H, d), 8.52 (1H, dd), 8.40 (1H, d), 7.80 (1H,dd), 7.39 (1H, dd), 4.06 (3H, s), 2.97 (2H, q), 1.34 (3H, t).

Production Examples 7 and 8

To a mixture of2-(3-ethylsulfanyl-pyridin-2-yl)-3-methyl-6-pentafluoroethyl-3H-imidazo[4,5-b]pyridine(254 mg) and chloroform (10 ml) was added m-chloroperbenzoic acid(purity: not less than 65%) (266 mg) while ice-cooling. The mixture washeated to room temperature and then stirred for 0.5 hours. To themixture were poured saturated aqueous sodium hydrogen carbonate solutionand saturated aqueous sodium thiosulfate solution, and the mixture wasextracted with chloroform. The organic layer was dried over magnesiumsulfate and concentrated under reduced pressure. The residue wassubjected to silica gel column chromatography to give 2-(3-ethanesulfinyl-pyridin-2-yl)-3-methyl-6-pentafluoroethyl-3H-imidazo[4,5-b]pyridine(8 mg), which is hereinafter referred to as “the present compound 7”),and2-(3-ethanesulfonyl-pyridin-2-yl)-3-methyl-6-pentafluoroethyl-3H-imidazo[4,5-b]pyridine(235 mg), which is hereinafter referred to as “the present compound 8”.

The Present Compound 7

¹H-NMR (CDCl₃) δ: 8.85 (1H, dd), 8.72 (1H, d), 8.68 (1H, dd), 8.31 (1H,d), 7.69 (1H, dd), 4.36 (3H, s), 3.72-3.61 (1H, m), 3.17-3.06 (1H, m),1.47 (3H, t).

The Present Compound 8

¹H-NMR (CDCl₃) δ: 9.00 (1H, dd), 8.72 (1H, d), 8.55 (1H, dd), 8.30 (1H,d), 7.73 (1H, dd), 3.89 (3H, s), 3.84 (2H, q), 1.37 (3H, t).

Production Example 9 (1)

To a mixture of 5-iodo-N²-methyl-pyridin-2,3-diamine (1.9 g) andpyridine (6 ml) were added WSC (1.28 g), HOBt (86 mg) and3-chloro-pyridin-2-carboxylic acid (1.3 g), and the mixture was stirredat room temperature for 9 hours. To this reaction mixture was addedwater, and the mixture was filtered to collect the precipitated powder.The collected powder was washed with chloroform to give3-chloro-pyridin-2-carboxylic acid(5-iodo-2-methylamino-pyridin-3-yl)-amide (3.6 g), which is hereinafterreferred to as “intermediate compound (M20-7)”.

Intermediate Compound (M20-7)

¹H-NMR (DMSO-d⁶) δ: 9.95 (1H, s), 8.65 (1H, d), 8.15-8.10 (2H, m), 8.00(1H, d), 7.65 (1H, dd), 6.30 (1H, d), 2.81 (3H, d).

Production Example 9 (2)

A mixture of the intermediate compound (M20-7) (3.4 g),p-toluenesulfonic acid monohydrate (5.8 g), DMF (30 ml) and toluene (120ml) was stirred while heating to 130° C. for 12 hours. After allowing tocool to room temperature, to the mixture was poured saturated aqueoussodium hydrogen carbonate solution, and the mixture was extracted withethyl acetate. The organic layer was dried over sodium sulfate, andconcentrated under reduced pressure. The residue was subjected to silicagel column chromatography to give2-(3-chloro-pyridin-2-yl)-6-iodo-3-methyl-3H-imidazo[4,5-b]pyridine (2.0g), which is hereinafter referred to as “intermediate compound (M6-7)”.

Intermediate Compound (M6-7)

¹H-NMR (CDCl₃) δ: 8.70 (1H, d), 8.66-8.63 (1H, m), 8.47-8.44 (1H, m),7.95 (1H, d), 7.45 (1H, dd), 3.90 (3H, s).

Production Example 9 (3)

A mixture of the intermediate compound (M6-7) (2.0 g), sodiumethanethiolate (888 mg) and DMF (45 ml) was stirred while heating at 50°C. for 12 hours. After allowing to cool to room temperature, to themixture was poured saturated aqueous sodium hydrogen carbonate solution,and the mixture was extracted with ethyl acetate. The organic layer wasdried over sodium sulfate, and concentrated under reduced pressure. Theresidue was subjected to silica gel column chromatography to give2-(3-ethylsulfanyl-pyridin-2-yl)-6-iodo-3-methyl-3H-imidazo[4,5-b]pyridine(1.0 g), which is hereinafter referred to as “the present compound 9”.

The Present Compound 9

¹H-NMR (CDCl₃) δ: 8.61 (1H, d), 8.51 (1H, dd), 8.45 (1H, d), 7.76 (1H,dd), 7.37 (1H, dd), 3.96 (3H, s), 2.94 (2H, q), 1.33 (3H, t).

Production Example 10 (1)

A mixture of 3-amino-5-trifluoromethylpyridin-2-thiol (0.45 g),3-chloro-5-trifluoromethylpyridin-2-carboxylic acid (0.55 g), WSC (0.67g), HOBt (31 mg) and pyridine (4.5 ml) was stirred at 60° C. for 4hours. To the cooled reaction mixture was added water, and the mixturewas extracted with ethyl acetate. The organic layer was washed withwater, dried over anhydrous magnesium sulfate, and concentrated underreduced pressure to give intermediate compound (M20-9).

Intermediate Compound (M20-9)

A mixture of the resulting intermediate compound (M20-9) (total amount),p-toluenesulfonic acid monohydrate (1.04 g) and N-methylpyrrolidinone(3.5 ml) was stirred while heating to 150° C. for 2 hours. To the cooledreaction mixture was added saturated aqueous sodium hydrogen carbonatesolution, and extracted with ethyl acetate. The organic layer was washedwith water, dried over anhydrous magnesium sulfate, and concentratedunder reduced pressure. The resulting residue was subjected to silicagel column chromatography to give2-(3-chloro-5-trifluoromethylpyridin-2-yl)-6-(trifluoromethyl)thiazolo[5,4-b]pyridine(0.29 g), which is hereinafter referred to as “intermediate compound.(M6-9)”.

Intermediate Compound (M6-9)

¹H-NMR (CDCl₃) δ: 8.94 (1H, d), 8.90 (1H, d), 8.69 (1H, d), 8.19 (1H,d).

Production Example 10 (2)

2-(3-ethylsulfanyl-5-trifluoromethylpyridin-2-yl)-6-(trifluoromethyl)thiazolo[5,4-b]pyridine(hereinafter referred to as “the present compound 10”) was synthesizedin the same manner as in Production Example 4 (2) except for using theintermediate compound (M6-9) instead of2-(3-chloro-5-trifluoromethylpyridin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine.

The Present Compound 10

¹H-NMR (CDCl₃) δ: 8.91 (1H, d), 8.70-8.67 (2H, m), 7.91 (1H, s), 3.09(2H, q), 1.51 (3H, t).

Production Example 11

2-(3-ethylsulfonyl-5-trifluoromethylpyridin-2-yl)-6-(trifluoromethyl)thiazolo[5,4-b]pyridine (hereinafter referred to as “the presentcompound 11”) was synthesized in the same manner as in ProductionExample 5 except for using2-(3-ethylsulfanyl-5-trifluoromethylpyridin-2-yl)-6-(trifluoromethyl)thiazolo[5,4-b]pyridineinstead of2-(3-ethylsulfanyl-5-trifluoromethylpyridin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine.

The Present Compound 11

¹H-NMR (CDCl₃) δ: 9.19 (1H, d), 8.98 (1H, d), 8.89 (1H, d), 8.61 (1H,d), 4.17 (2H, q), 1.49 (3H, t).

Production Example 12 (1)

A mixture of 3-amino-5-trifluoromethylpyridin-2-thiol (0.45 g),3-chloropyridin-2-carboxylic acid (0.39 g), WSC (0.67 g), HOBt (31 mg)and pyridine (4 ml) was stirred at room temperature for 12 hours. To thereaction mixture was added water, and the mixture was filtered tocollect a solid. The resulting solid was washed with water, followed byn-hexane, and dried to give 3-chloropyridin-2-carboxylic acid(2-mercapto-5-trifluoromethylpyridin-3-yl)-amide (0.45 g), which ishereinafter referred to as “intermediate compound (M20-11)”.

Intermediate Compound (M20-11)

Production Example 12 (2)

A mixture of the intermediate compound (M20-11) (0.45 g),p-toluenesulfonic acid monohydrate (0.70 g) and NMP (4 ml) was stirredat 150° C. for 2 hours. To the cooled reaction mixture was addedsaturated aqueous sodium hydrogen carbonate solution, and extracted withethyl acetate. The organic layer was washed with water, dried overanhydrous magnesium sulfate, and concentrated under reduced pressure.The resulting residue was subjected to silica gel column chromatographyto give2-(3-chloropyridin-2-yl)-6-(trifluoromethyl)thiazolo[5,4-b]pyridine(0.47 g), which is hereinafter referred to as “intermediate compound(M6-11)”.

Intermediate Compound (M6-11)

Production Example 12 (3)

2-(3-ethylsulfanyl-2-yl)-6-(trifluoromethyl)thiazolo[5,4-b]pyridine(hereinafter referred to as “the present compound 41”) was synthesizedin the same manner as in Production Example 1 (2) except for using theintermediate compound (M6-11) instead of2-(3-fluoropyridin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine.

The Present Compound 41

¹H-NMR (CDCl₃) δ: 8.87 (1H, d), 8.64 (1H, d), 8.48 (1H, dd), 7.76 (1H,dd), 7.37 (1H, dd), 3.06 (2H, q), 1.49 (3H, t).

Production Example 12 (4)

To a mixture of2-(3-ethylsulfanyl-2-yl)-6-(trifluoromethyl)thiazolo[5,4-b]pyridine(0.36 g) and chloroform (5 ml) was added m-chloroperbenzoic acid(purity: not less than 65%) (0.56 g), and the mixture was stirred atroom temperature for 12 hours. To the reaction mixture were pouredaqueous 10% sodium thiosulfate solution and saturated aqueous sodiumhydrogen carbonate solution, and the mixture was extracted withchloroform. The organic layer was washed with water, dried overanhydrous magnesium sulfate, and concentrated under reduced pressure togive 2-(3-ethylsulfonyl-2-yl)-6-(trifluoromethyl)thiazolo[5,4-b]pyridine(0.27 g), which is hereinafter referred to as “the present compound 12”,and 2-(3-ethylsulfonyl-2-yl)-6-(trifluoromethyl)thiazolo[5,4-b]pyridine4-oxide (91 mg), which is hereinafter referred to as “the presentcompound 22”.

The Present Compound 12

¹H-NMR (CDCl₃) δ: 8.98-8.93 (2H, m), 8.66 (1H, dd), 8.57 (1H, d), 7.69(1H, dd), 4.13 (2H, q), 1.45 (3H, t).

The Present Compound 22

¹H-NMR (CDCl₃) δ: 8.96 (1H, dd), 8.68 (1H, dd), 8.62 (1H, s), 8.20 (1H,s), 7.74 (1H, dd), 4.06 (2H, q), 1.44 (3H, t).

Production Example 13 (1)

A mixture of2-(3-ethylsulfanyl-pyridin-2-yl)-6-iodo-3-methyl-3H-imidazo[4,5-b]pyridine(1.1 g), copper iodide (160 mg), sodium sulfide 9-hydrate (2.7 g) andDMF (10 ml) was stirred at 110° C. for 5 hours. To the reaction mixturewas added water, and the mixture was extracted with ethyl acetate. Theorganic layer was dried over sodium sulfate, and concentrated underreduced pressure. The residue was subjected to silica gel columnchromatography to give a compound represented by the formula

(710 mg), which is hereinafter referred to as “intermediate compound(P9′-1)”.

Intermediate Compound (P9′-1)

¹H-NMR (DMSO-D₆) δ: 8.56-8.55 (2H, m), 8.53-8.50 (2H, m), 8.38-8.36 (2H,m), 8.04 (2H, d), 7.61-7.56 (2H, m), 3.87 (6H, brs), 3.00 (4H, q),1.23-1.16 (6H, m).

Production Example 13 (2)

A mixture of the intermediate compound (P9′-1) (710 mg) and DMF (12 ml)was cooled to −60° C., and thereto was added trifluoroiodomethane (10g). To this mixture was added dropwise tetrakis(dimethylamino)ethylene(1.2 ml) at −40° C. The mixture was warmed to −10° C., and stirred at−10° C. for 5 hours. To the reaction mixture was added water, and themixture was extracted with ethyl acetate. The organic layer was driedover sodium sulfate, and concentrated under reduced pressure. Theresidue was subjected to silica gel column chromatography to give2-(3-ethylsulfanyl-pyridin-2-yl)-3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridine(530 mg), which is hereinafter referred to as “the present compound 13”.

The Present Compound 13

¹H-NMR (CDCl₃) δ: 8.67 (1H, d), 8.52 (1H, dd), 8.46 (1H, d), 7.79 (1H,dd), 7.39 (1H, dd), 4.03 (3H, s), 2.97 (2H, q), 1.36 (3H, t).

Production Examples 14 and 15

A mixture of2-(3-ethylsulfanyl-pyridin-2-yl)-3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridine(200 mg), m-chloroperbenzoic acid (purity: not less than 65%) (230 mg)and chloroform (10 ml) was stirred while ice-cooling for 5 hours. To thereaction mixture was poured saturated aqueous sodium hydrogen carbonatesolution, and the mixture was extracted with chloroform. The organiclayer was dried over sodium sulfate, and concentrated under reducedpressure. The residue was subjected to silica gel column chromatographyto give2-(3-ethylsulfinyl-pyridin-2-yl)-3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridine(89 mg), which is hereinafter referred to as “the present compound 14”,and2-(3-ethylsulfonyl-pyridin-2-yl)-3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridine(130 mg), which is hereinafter referred to as “the present compound 15”.

The Present Compound 14

¹H-NMR (CDCl₃) δ: 8.87-8.83 (1H, m), 8.73-8.64 (2H, m), 8.41 (1H, d),7.72-7.66 (1H, m), 4.34 (3H, s), 3.72-3.62 (1H, m), 3.17-3.05 (1H, m),1.47 (3H, t).

The Present Compound 15

¹H-NMR (CDCl₃) δ: 9.01-8.98 (1H, m), 8.71 (1H, d), 8.55-8.52 (1H, m),8.39 (1H, d), 7.72 (1H, dd), 3.90-3.81 (5H, m), 1.36 (3H, t).

Production Example 16

To a mixture of2-(3-ethylsulfanyl-pyridin-2-yl)-3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridine(270 mg), sodium tungstate dihydrate (110 mg), and acetonitrile (5 ml)was added 30% hydrogen peroxide solution (2 ml) at 40° C. The mixturewas heated to 80° C. and then stirred for 24 hours. To the mixture wasadded saturated aqueous sodium thiosulfate solution, and the mixture wasextracted with ethyl acetate. The organic layer was dried over sodiumsulfate, and concentrated under reduced pressure. The residue wassubjected to silica gel column chromatography to give2-(3-ethylsulfonyl-pyridin-2-yl)-3-methyl-6-trifluoromethylsulfonyl-3H-imidazo[4,5-b]pyridine(280 mg), which is hereinafter referred to as “the present compound 16”.

The Present Compound 16

¹H-NMR (CDCl₃) δ: 9.08 (1H, d), 9.04 (1H, dd), 8.71 (1H, d), 8.57 (1H,dd), 7.79 (1H, dd), 3.93 (3H, s), 3.82 (2H, q), 1.38 (3H, t).

Production Example 17 (1)

A mixture of N²-methyl-5-pentafluoroethyl-pyridin-2,3-diamine (590 mg),3-chloro-5-trifluoromethyl-pyridin-2-carboxylic acid (560 mg), WSC (520mg), HOBt (35 mg), and pyridine (5 ml) was stirred at room temperaturefor 5 hours. To the reaction mixture was added water, and the mixturewas extracted with ethyl acetate. The organic layer was dried oversodium sulfate, and concentrated under reduced pressure to giveintermediate compound (M20-17).

Intermediate Compound (M20-17)

The resulting intermediate compound (M20-17) was dissolved in a mixedsolvent of DMF (7.5 ml) and toluene (30 ml), thereto was addedp-toluenesulfonic acid monohydrate (1.5 g), and the mixture was stirredat 160° C. for 6 hours. The reaction mixture was allowed to cool to roomtemperature, thereto was poured saturated aqueous sodium hydrogencarbonate solution, and the mixture was extracted with t-butylmethylether. The organic layer was dried over sodium sulfate, and concentratedunder reduced pressure. The residue was subjected to silica gel columnchromatography to give2-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-3-methyl-6-pentafluoroethyl-3H-imidazo[4,5-b]pyridine(540 mg), which is hereinafter referred to as “intermediate compound(M6-17)”.

Intermediate Compound (M6-17)

¹H-NMR (CDCl₃) δ: 8.96 (1H, d), 8.74 (1H, d), 8.40 (1H, d), 8.23 (1H,d), 4.03 (3H, s).

Production Example 17 (2)

2-(3-ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl)-3-methyl-6-pentafluoroethyl-3H-imidazo[4,5-b]pyridine(hereinafter referred to as “the present compound 17”) was synthesizedin the same manner as in Production Example 1 (2) except for using theintermediate compound (M6-17) instead of2-(3-fluoropyridin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine.

The Present Compound 17

¹H-NMR (CDCl₃) δ: 8.75 (1H, d), 8.71 (1H, d), 8.42 (1H, d), 7.93 (1H,d), 4.12 (3H, s), 3.03 (2H, q), 1.41 (3H, t).

Production Examples 18 and 19

2-(3-ethylsulfinyl-5-trifluoromethyl-pyridin-2-yl)-3-methyl-6-pentafluoroethyl-3H-imidazo[4,5-b]pyridine(hereinafter referred to as “the present compound 18”) and2-(3-ethylsulfonyl-5-trifluoromethyl-pyridin-2-yl)-3-methyl-6-pentafluoroethyl-3H-imidazo[4,5-b]pyridine(hereinafter referred to as “the present compound 19”) were synthesizedin the same manner as in Production Examples 2 and 3 except for using2-(3-ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl)-3-methyl-6-pentafluoroethyl-3H-imidazo[4,5-b]pyridineinstead of 2-(3-ethylsulfanylpyridin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine.

The Present Compound 18

¹H-NMR (CDCl₃) δ: 9.10 (1H, d), 8.94 (1H, d), 8.76 (1H, d), 8.36 (1H,d), 4.41 (3H, s), 3.76-3.66 (1H, m), 3.18-3.07 (1H, m), 1.49 (3H, t).

The Present Compound 19

¹H-NMR (CDCl₃) δ: 9.27 (1H, d), 8.80 (1H, d), 8.76 (1H, s), 8.34 (1H,s), 4.01-3.94 (5H, m), 1.41 (3H, t).

Production Example 20

To a mixture of2-(3-ethylsulfonyl-pyridin-2-yl)-3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridine(500 mg) and chloroform (10 ml) was added m-chloroperbenzoic acid(purity: not less than 65%) (429 mg) while ice-cooling, and the mixturewas stirred at room temperature for 1 hour and at 50° C. for 2 hours. Tothe reaction mixture were poured aqueous sodium thiosulfate solution andaqueous sodium hydrogen carbonate solution, and the mixture wasextracted with chloroform. The organic layer was dried over sodiumsulfate, and concentrated under reduced pressure. The residue wassubjected to silica gel column chromatography to give2-(3-ethylsulfonyl-pyridin-2-yl)-3-methyl-6-trifluoromethylsulfinyl-3H-imidazo[4,5-b]pyridine(353 mg), which is hereinafter referred to as “the present compound 20”.

The Present Compound 20

¹H-NMR (CDCl₃) δ: 9.02 (1H, dd), 8.77 (1H, d), 8.60-8.52 (2H, m), 7.75(1H, dd), 3.91 (3H, s), 3.83 (2H, q), 1.38 (3H, t).

Production Example 21 (1)

To a mixture of 4-iodo-2-nitro-phenyl amine (2.0 g), 60% sodium hydride(oil) (330 mg), and DMF (20 ml) was added dropwise iodomethane (470 μL)while ice-cooling. The reaction mixture was heated to room temperature,and then stirred for 2 hours. To the reaction mixture was added water,and the mixture was extracted with ethyl acetate. The organic layer wasdried over sodium sulfate, and concentrated under reduced pressure. Theresidue was subjected to silica gel column chromatography to give(4-iodo-2-nitro-phenyl)-methyl-amine (2.0 g).

Production Example 21 (2)

A mixture of an iron powder (1.7 g), acetic acid (2.2 ml), ethanol (80ml), and water (25 ml) was stirred at 70° C. To the reaction mixture wasadded dropwise a mixture of (4-iodo-2-nitro-phenyl)-methyl-amine (2.0 g)and ethanol (20 ml). After that, the mixture was stirred at 70° C. for 6hours. Then, the reaction mixture was filtrated and thoroughly washedwith THF. The resulting filtrate was concentrated under reducedpressure. To the resulting residue was poured saturated aqueous sodiumhydrogen carbonate solution, and the mixture was extracted with ethylacetate. The organic layer was dried over sodium sulfate, andconcentrated under reduced pressure. The residue was subjected to silicagel column chromatography to give 4-iodo-N¹-methyl-benzene-1,2-diamine(1.6 g).

Production Example 21 (3)

A mixture of 4-iodo-N¹-methyl-benzene-1,2-diamine (850 mg),3-chloro-pyridin-2-carboxylic acid (590 mg), WSC (790 mg), HOBt (46 mg),and pyridine (10 ml) was stirred at 100° C. for 12 hours. To thereaction mixture was added water, and the mixture was extracted withethyl acetate. The organic layer was dried over sodium sulfate, andconcentrated under reduced pressure. The residue was subjected to silicagel column chromatography to give2-(3-chloro-pyridin-2-yl)-5-iodo-1-methyl-1H-benzimidazole (930 mg),which is hereinafter referred to as “intermediate compound (M6-21)”.

Intermediate Compound (M6-21)

Production Example 21 (4)

2-(3-ethylsulfanyl-pyridin-2-yl)-5-iodo-1-methyl-1H-benzimidazole(hereinafter referred to as “the present compound 21”) was synthesizedin the same manner as in Production Example 1 (2) except for using theintermediate compound (M6-21) instead of2-(3-fluoropyridin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine.

The Present Compound 21

¹H-NMR (CDCl₃) δ: 8.49 (1H, dd), 8.22 (1H, d), 7.75 (1H, d), 7.62 (1H,dd), 7.35 (1H, dd), 7.21 (1H, d), 3.87 (3H, s), 2.92 (2H, q), 1.32 (3H,t).

Production Example 22 (1)

A mixture of 4-amino phenyl sulfur pentafluoride (5.2 g), acetic acidanhydride (2.7 ml), triethylamine (6.6 ml) and chloroform (20 ml) wasstirred at room temperature for 3 hours. To the reaction mixture waspoured water, and the mixture was extracted with chloroform. Theresulting residue was subjected to recrystallization with hexane andethyl acetate to give 4-acetoamide phenyl sulfur pentafluoride (5.4 g).

Production Example 22 (2)

To a mixture of 4-acetoamide phenyl sulfur pentafluoride (5.4 g) andsulfuric acid (15 ml) was added dropwise fuming nitric acid (905 ml)while ice-cooling. After that, the mixture was stirred at roomtemperature for 3 hours. The reaction mixture was poured onto ice, andthe precipitated crystal was collected by filtration. The crystal waswashed with water and dried to give 4-amino-3-nitro phenyl sulfurpentafluoride (5.2 g).

Production Example 22 (3)

To a mixture of 4-amino-3-nitro-phenyl sulfur pentafluoride (2.0 g), 60%sodium hydride (oil) (310 mg) and DMF (15 ml) was added dropwiseiodomethane (447 μL) while ice-cooling. After that, the mixture wasstirred at room temperature for 3 hours. To the reaction mixture waspoured water, and the precipitated solid was collected by filtration.The solid was washed with water and dried to givemethyl-(2-nitro-4-pentafluorosulfanyl-phenyl)-amine (2.0 g).

¹H-NMR (CDCl₃) δ: 8.60 (1H, d), 8.28 (1H, brs), 7.78 (1H, dd), 6.89 (1H,d), 3.10 (3H, d).

Production Example 22 (4)

N¹-methyl-4-pentafluorosulfanyl-benzene-1,2-diamine was synthesized inthe same manner as in Production Example 21 (2) except for usingmethyl-(2-nitro-4-pentafluorosulfanyl-phenyl)-amine instead of(4-iodo-2-nitro-phenyl)-methyl-amine.

Production Example 22 (5)

3-chloro-pyridin-2-carboxylic acid(2-methylamino-5-pentafluorosulfanyl-phenyl)-amide (hereinafter referredto as “intermediate compound (M20-23)”) was synthesized in the samemanner as in Production Example 9 (1) except for usingN¹-methyl-4-pentafluorosulfanyl-benzene-1,2-diamine instead of5-iodo-N²-methyl-pyridin-2,3-diamine.

Intermediate Compound (M20-23)

¹H-NMR (CDCl₃) δ: 9.57 (1H, s), 8.55 (1H, dd), 7.91 (1H, dd), 7.81 (1H,d), 7.59 (1H, dd), 7.50-7.45 (1H, m), 6.71 (1H, d), 4.52 (1H, d), 2.93(3H, d).

Production Example 22 (6)

To a mixture of the intermediate compound (M20-23) (405 mg) and DMF (10ml) was added sodium ethanethiolate (193 mg) while ice-cooling, and thenthe mixture was stirred at room temperature for 8 hours and 60° C. for 2hours. To the reaction mixture was added water, and the mixture wasextracted with ethyl acetate. The organic layer was washed with water,dried over anhydrous magnesium sulfate, and concentrated under reducedpressure. The resulting residue was subjected to silica gel columnchromatography to give2-(3-ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl)-1-methyl-5-pentafluorosulfanyl-1H-benzimidazole(411 mg), which is hereinafter referred to as “the present compound 23”.

The Present Compound 23

¹H-NMR (CDCl₃) δ: 8.50 (1H, dd), 8.33 (1H, d), 7.79-7.74 (2H, m),7.46-7.43 (1H, m), 7.37 (1H, dd), 3.92 (3H, s), 2.94 (2H, q), 1.33 (3H,t).

Production Example 23

2-(3-ethylsulfonyl-pyridin-2-yl)-1-methyl-5-pentafluorosulfanyl-1H-benzimidazole(hereinafter referred to as “the present compound 24”) was synthesizedin the same manner as in Production Example 11 except for using2-(3-ethylsulfanyl-pyridin-2-yl)-1-methyl-5-pentafluorosulfanyl-1H-benzimidazoleinstead of2-(3-ethylsulfanyl-5-trifluoromethylpyridin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine.

The Present Compound 24

¹H-NMR (CDCl₃) δ: 8.96 (1H, dd), 8.50 (1H, dd), 8.24 (1H, d), 7.79 (1H,dd), 7.68 (1H, dd), 7.48 (1H, d), 3.82 (2H, q), 3.75 (3H, s), 1.34 (3H,t).

Production Example 24 (1)

3-chloro-5-trifluoromethyl-pyridin-2-carboxylic acid(5-iodo-2-methylamino-pyridin-3-yl)-amide (hereinafter referred to as“intermediate compound (M20-35)”) was synthesized in the same manner asin Production Example 9 (1) except for using3-chloro-5-trifluoromethyl-pyridin-2-carboxylic acid instead of3-chloro-pyridin-2-carboxylic acid.

Intermediate Compound (M20-35)

¹H-NMR (CDCl₃) δ: 9.33 (1H, s), 8.80 (1H, d), 8.28 (1H, d), 8.17 (1H,d), 8.00 (1H, d), 4.60 (1H, s), 3.01 (3H, d).

Production Example 24 (2)

2-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-6-iodo-3-methyl-3H-imidazo[4,5-b]pyridine(hereinafter referred to as “intermediate compound (M6-35)”) wassynthesized in the same manner as in Production Example 9 (2) except forusing the intermediate compound (M20-35) instead of3-chloro-pyridin-2-carboxylic acid(5-iodo-2-methylamino-pyridin-3-yl)-amide.

Intermediate Compound (M6-35)

¹H-NMR (CDCl₃) δ: 8.95 (1H, s), 8.68 (1H, s), 8.49 (1H, s), 8.20 (1H,s), 3.95 (3H, s).

Production Example 24 (3)

2-(3-ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl)-6-iodo-3-methyl-3H-imidazo[4,5-b]pyridine(hereinafter referred to as “the present compound 42”) was synthesizedin the same manner as in Production Example 1 (2) except for using theintermediate compound (M6-35) instead of2-(3-fluoropyridin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine.

The Present Compound 42

¹H-NMR (CDCl₃) δ: 8.73 (1H, s), 8.65 (1H, d), 8.49 (1H, d), 7.91 (1H,s), 4.04 (3H, s), 3.01 (2H, q), 1.39 (3H, t).

Production Example 24 (4)

A mixture of2-(3-ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl)-6-iodo-3-methyl-3H-imidazo[4,5-b]pyridine(900 mg), thiobenzoic acid 3 (20 μL), copper iodide (45 mg),1,10-phenanthroline (85 mg), diisopropylethylamine (940 μL), and toluene(25 ml) was stirred at 110° C. for 8 hours. To the reaction mixture wasadded water, and the mixture was extracted with ethyl acetate. Theorganic layer was dried over sodium sulfate, and concentrated underreduced pressure. The residue was subjected to silica gel columnchromatography to give thiobenzoic acidS-[2-(3-ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridine]ester(990 mg).

¹H-NMR (CDCl₃) δ: 8.74 (1H, s), 8.54 (1H, d), 8.33 (1H, d), 8.07 (2H,dd), 7.92 (1H, s), 7.63 (1H, t), 7.51 (2H, t), 4.10 (3H, s), 3.01 (2H,q), 1.39 (3H, t).

Production Example 24 (5)

A mixture of thiobenzoic acidS-[2-(3-ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridine]ester(1.8 g), potassium carbonate (1.1 g), and methanol (20 ml) was stirredat room temperature for 4.5 hours. To the reaction mixture was pouredsaturated aqueous ammonium chloride solution, and the mixture wasextracted with ethyl acetate. The organic layer was washed withsaturated aqueous sodium hydrogen carbonate solution, dried over sodiumsulfate, and concentrated under reduced pressure to give2-(3-ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridin-6-thiol(1.2 g), which is hereinafter referred to as “the present compound 43”.

The Present Compound 43

¹H-NMR (CDCl₃) δ: 8.73 (1H, s), 8.46 (1H, d), 8.19 (1H, d), 7.90 (1H,s), 4.04 (3H, s), 3.01 (2H, q), 1.39 (3H, t).

Production Example 24 (6)

To a mixture of2-(3-ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridin-6-thiol(1.2 g), iodine (20 mg), and DMF (30 ml) was stirred at room temperatureunder air atmosphere for 12 hours. The reaction mixture wasconcentrated, and then the residue was subjected to silica gel columnchromatography to give a compound represented by the formula:

(800 mg), which is hereinafter referred to as “intermediate compound(P9′-4)”.

Intermediate Compound (P9′-4)

¹H-NMR (CDCl₃) δ: 8.73 (2H, s), 8.52 (2H, d), 8.35, (2H, d), 7.91 (2H,d), 4.06 (6H, s), 3.04-2.98 (4H, m), 1.39 (6H, t).

Production Example 24 (7)

2-(3-ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl)-3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridine(hereinafter referred to as “the present compound 28”) was synthesizedin the same manner as in Production Example 13 (2) except for using theintermediate compound (P9′-4) instead of the intermediate compound(P9′-1).

The Present Compound 28

¹H-NMR (CDCl₃) δ: 8.75 (1H, d), 8.71 (1H, d), 8.50 (1H, d), 7.93 (1H,d), 4.10 (3H, s), 3.03 (2H, q), 1.41 (3H, t).

Production Example 24 (8)

To a mixture of2-(3-ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl)-3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridine(299 mg) and chloroform (30 ml) was added m-chloroperbenzoic acid(purity: not less than 65%) (0.34 g) while ice-cooling, and the mixturewas stirred while ice-cooling for 5 hours. To the reaction mixture werepoured saturated aqueous sodium hydrogen carbonate solution andsaturated aqueous sodium thiosulfate solution, and the mixture wasextracted with chloroform. The organic layer was dried over magnesiumsulfate and concentrated under reduced pressure. The resulting residuewas subjected to silica gel column chromatography to give2-(3-ethylsulfonyl-5-trifluoromethyl-pyridin-2-yl)-3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridine(0.24 g), which is hereinafter referred to as “the present compound 44”.

The Present Compound 44

¹H-NMR (CDCl₃) δ: 9.24 (1H, d), 8.79 (1H, d), 8.74 (1H, d), 8.40 (1H,d), 3.97 (2H, q), 3.93 (3H, s), 1.42 (3H, t).

Production Example 24 (9)

2-(3-ethylsulfonyl-5-trifluoromethyl-pyridin-2-yl)-3-methyl-6-trifluoromethylsulfonyl-3H-imidazo[4,5-b]pyridine(hereinafter referred to as “the present compound 25”) was synthesizedin the same manner as in Production Example 16 except for using2-(3-ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl)-3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridineinstead of2-(3-ethylsulfanyl-pyridin-2-yl)-3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridine.

The Present Compound 25

¹H-NMR (CDCl₃) δ: 9.28 (1H, d), 9.10 (1H, d), 8.80 (1H, d), 8.72 (1H,d), 3.98 (3H, s), 3.93 (2H, q), 1.43 (3H, t).

Production Example 25

A mixture of2-(3-ethylsulfanyl-pyridin-2-yl)-5-iodo-1-methyl-1H-benzimidazole (340mg), copper iodide (410 mg), sodium pentafluoropropionate (800 mg), NMP(5 ml), and xylene (5 ml) was stirred at 160° C. for 5 hours. Thereaction mixture was allowed to cool to room temperature, and thensaturated aqueous sodium hydrogen carbonate solution and 28% ammoniasolution were poured thereto. Then, the mixture was extracted witht-butylmethyl ether. The organic layer was dried over sodium sulfate,and concentrated under reduced pressure. The residue was subjected tosilica gel column chromatography to give2-(3-ethylsulfanyl-pyridin-2-yl)-1-methyl-5-pentafluoroethyl-1H-benzimidazole(240 mg), which is hereinafter referred to as “the present compound 26”.

The Present Compound 26

¹H-NMR (CDCl₃) δ: 8.50 (1H, dd), 8.16 (1H, s), 7.77 (1H, dd), 7.57 (1H,d), 7.53 (1H, d), 7.36 (1H, dd), 3.93 (3H, s), 2.94 (2H, q), 1.33 (3H,t).

Production Example 26

2-(3-ethylsulfonyl-pyridin-2-yl)-1-methyl-5-pentafluoroethyl-1H-benzimidazole(hereinafter referred to as “the present compound 27”) was synthesizedin the same manner as in Production Example 5 except for using2-(3-ethylsulfanyl-pyridin-2-yl)-1-methyl-5-pentafluoroethyl-H-benzimidazoleinstead of2-(3-ethylsulfanyl-5-trifluoromethylpyridin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine.

The Present Compound 27

¹H-NMR (CDCl₃) δ: 8.98 (1H, dd), 8.53 (1H, dd), 8.06 (1H, s), 7.70 (1H,dd), 7.60 (1H, d), 7.56 (1H, d), 3.86-3.78 (5H, m), 1.34 (3H, t).

Production Example 27

To a mixture of2-(3-ethylsulfanyl-5-trifluoromethylpyridin-2-yl)-3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridine(0.18 g) and chloroform (4 ml) was added m-chloroperbenzoic acid(purity: not less than 65%) (0.21 g) while ice-cooling, and then themixture was stirred while ice-cooling for 5 minutes. To the reactionmixture were poured saturated aqueous sodium hydrogen carbonate solutionand saturated aqueous sodium thiosulfate solution, and the mixture wasextracted with chloroform. The organic layer was dried over magnesiumsulfate, and concentrated under reduced pressure. The resulting residuewas subjected to silica gel column chromatography to give2-(3-ethylsulfanyl-5-trifluoromethylpyridin-2-yl)-3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridine(0.16 g), which is hereinafter referred to as “the present compound 29”.

The Present Compound 29

¹H-NMR (CDCl₃) δ: 9.10-9.07 (1H, m), 8.94-8.91 (1H, m), 8.77-8.74 (1H,m), 8.46-8.44 (1H, m), 4.38 (3H, s), 3.76-3.65 (1H, m), 3.16-3.05 (1H,m), 1.49 (3H, t).

Production Example 28 (1)

3-chloro-pyridin-2-carboxylic acid(2-methylamino-5-trifluoromethyl-phenyl)-amide (hereinafter referred toas “intermediate compound (M20-29)”) was synthesized in the same manneras in Production Example 9 (1) except for usingN¹-methyl-4-trifluoromethyl-benzene-1,2-diamine instead of5-iodo-N²-methyl-pyridin-2,3-diamine.

Intermediate Compound (M20-29)

¹H-NMR (CDCl₃) δ: 9.56 (1H, s), 8.55-8.54 (1H, m), 7.91 (1H, dd), 7.70(1H, d), 7.49-7.43 (3H, m), 6.79 (1H, d), 2.93 (3H, d).

Production Example 28 (2)

A mixture of the intermediate compound (M20-29) (800 mg), sodiumethanethiolate (350 mg), and DMF (10 ml) was stirred at 100° C. for 5hours. To the reaction mixture was added saturated aqueous sodiumhydrogen carbonate solution, and then the mixture was extracted withethyl acetate. The organic layer was dried over sodium sulfate, andconcentrated under reduced pressure. The residue was subjected to silicagel column chromatography to give2-(3-ethylsulfanyl-pyridin-2-yl)-1-methyl-5-trifluoromethyl-H-benzimidazole(410 mg), which is hereinafter referred to as “the present compound 30”.

The Present Compound 30

¹H-NMR (CDCl₃) b: 8.51 (1H, dd), 8.17 (1H, d), 7.78 (1H, dd), 7.61 (1H,dd), 7.52 (1H, d), 7.38 (1H, dd), 3.93 (3H, s), 2.94 (2H, q), 1.33 (3H,t).

Production Example 29, 30

2-(3-ethylsulfinyl-pyridin-2-yl)-1-methyl-5-trifluoromethyl-1H-benzimidazole(hereinafter referred to as “the present compound 31”) and2-(3-ethylsulfonyl-pyridin-2-yl)-1-methyl-5-trifluoromethyl-1H-benzimidazole(hereinafter referred to as “the present compound 32”) were synthesizedin the same manner as in Production Examples 2 and 3 except for using2-(3-ethylsulfanyl-pyridin-2-yl)-1-methyl-5-trifluoromethyl-1H-benzimidazoleinstead of 2-(3-ethylsulfanylpyridin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine.

The Present Compound 31

¹H-NMR (CDCl₃) δ: 8.77 (1H, d), 8.61 (1H, d), 8.05 (1H, s), 7.61 (1H,dd), 7.55 (1H, d), 7.48 (1H, d), 4.20 (3H, s), 3.73-3.61 (1H, m),3.11-3.00 (1H, m), 1.47 (3H, t).

The Present Compound 32

¹H-NMR (CDCl₃) δ: 8.95 (1H, dd), 8.50 (1H, dd), 8.09 (1H, d), 7.66 (1H,dd), 7.61 (1H, d), 7.53 (1H, d), 3.83 (2H, q), 3.75 (3H, s), 1.33 (3H,t).

Production Example 31 (1)

3-chloro-5-trifluoromethyl-pyridin-2-carboxylic acid(2-methylamino-5-trifluoromethyl-phenyl)-amide (hereinafter referred toas “intermediate compound (M20-31)”) was synthesized in the same manneras in Production Example 9 (1) except for usingN¹-methyl-4-trifluoromethyl-benzene-1,2-diamine and3-chloro-5-trifluoromethylpyridin-2-carboxylic acid instead of5-iodo-N²-methyl-pyridin-2,3-diamine and 3-chloro-pyridin-2-carboxylicacid.

Intermediate Compound (M20-31)

¹H-NMR (CDCl₃) δ: 9.42 (1H, s), 8.80 (1H, d), 8.16 (1H, d), 7.71 (1H,s), 7.47 (1H, d), 6.81 (1H, d), 4.32 (1H, s), 2.93 (3H, d).

Production Example 31 (2)

2-(3-ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl)-1-methyl-5-trifluoromethyl-1H-benzimidazole(hereinafter referred to as “the present compound 33”) and3-ethylsulfanyl-5-trifluoromethyl-pyridin-2-carboxylic acid(2-methylamino-5-trifluoromethyl-phenyl)-amide (hereinafter referred toas “intermediate compound (M3-32)”) were synthesized in the same manneras in Production Example 28 (2) except for using the intermediatecompound (M20-31) instead of 3-chloro-pyridin-2-carboxylic acid(2-methylamino-5-trifluoromethyl-phenyl)-amide.

The Present Compound 33

¹H-NMR (CDCl₃) δ: 8.72 (1H, d), 8.21 (1H, d), 7.91 (1H, d), 7.63 (1H,d), 7.54 (1H, d), 4.00 (3H, s), 3.00 (2H, q), 1.38 (3H, t).

Intermediate Compound (M3-32)

¹H-NMR (CDCl₃) δ: 9.64 (1H, s), 8.53 (1H, d), 7.86 (1H, s), 7.76 (1H,d), 7.41 (1H, dd), 6.76 (1H, d), 4.35 (1H, d), 2.96 (2H, q), 2.90 (3H,d), 1.44 (3H, t).

Production Examples 32 and 33

2-(3-ethylsulfinyl-5-trifluoromethyl-pyridin-2-yl)-1-methyl-5-trifluoromethyl-1H-benzimidazole(hereinafter referred to as “the present compound 34”) and2-(3-ethylsulfonyl-5-trifluoromethyl-pyridin-2-yl)-1-methyl-5-trifluoromethyl-1H-benzimidazole(hereinafter referred to as “the present compound 35”) were synthesizedin the same manner as in Production Examples 2 and 3 except for using2-(3-ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl)-1-methyl-5-trifluoromethyl-1H-benzimidazoleinstead of 2-(3-ethylsulfanylpyridin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine.

The Present Compound 34

¹H-NMR (CDCl₃) δ: 9.05 (1H, d), 8.91 (1H, d), 8.12 (1H, d), 7.67 (1H,dd), 7.60 (1H, d), 4.32 (3H, s), 3.80-3.70 (1H, m), 3.15-3.05 (1H, m),1.51 (3H, t).

The Present Compound 35

¹H-NMR (CDCl₃) δ: 9.22 (1H, d), 8.77 (1H, d), 8.10 (1H, d), 7.66 (1H,dd), 7.57 (1H, d), 3.98 (2H, q), 3.84 (3H, s), 1.40 (3H, t).

Production Example 34, 35

To a mixture of2-(3-ethylsulfonylpyridin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine(550 mg) and chloroform (15 ml) was added m-chloroperbenzoic acid(purity; not less than 65%) (750 mg), and the mixture was heated underreflux for 20 hours. To the reaction mixture was poured aqueous 10%sodium thiosulfate solution, and the mixture was extracted withchloroform. The organic layer was washed with saturated aqueous sodiumhydrogen carbonate solution, dried over anhydrous magnesium sulfate, andconcentrated under reduced pressure. The resulting residue was subjectedto silica gel column chromatography to give 2-(3-ethylsulfonyl-1-oxypyridin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (168mg), which is hereinafter referred to as “the present compound 36” and2-(3-ethylsulfonylpyridin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine4-oxide (73 mg), which is hereinafter referred to as “the presentcompound 37”.

The Present Compound 36

¹H-NMR (CDCl₃) δ: 8.79 (1H, d), 8.54 (1H, dd), 8.33 (1H, d), 7.99 (1H,dd), 7.69 (1H, dd), 3.85-3.74 (4H, m), 3.52-3.42 (1H, m), 1.34 (3H, t).

The Present Compound 37

¹H-NMR (CDCl₃) b: 9.03 (1H, dd), 8.53 (1H, dd), 8.47 (1H, d), 7.92 (1H,d), 7.77 (1H, dd), 4.29 (3H, s), 3.69 (2H, q), 1.36 (3H, t).

Production Example 36 (1)

2-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-5-iodo-1-methyl-1H-benzimidazole(hereinafter referred to as “intermediate compound (M6-41)”) wassynthesized in the same manner as in Production Example 4 (1) except forusing 4-iodo-N¹-methyl-benzene-1,2-diamine instead ofN²-methyl-5-trifluoromethylpyridin-2,3-diamine.

Intermediate Compound (M6-41)

¹H-NMR (CDCl₃) δ: 8.92 (1H, d), 8.23 (1H, d), 8.17 (1H, d), 7.66 (1H,dd), 7.23 (1H, d), 3.85 (3H, s).

Production Example 36 (2)

2-(3-ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl)-5-iodo-1-methyl-1H-benzimidazole(hereinafter referred to as “the present compound 45”) was synthesizedin the same manner as in Production Example 1 (2) except for using theintermediate compound (M6-41) instead of2-(3-fluoropyridin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine.

The Present Compound 45

Production Example 36 (3)

2-(3-ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl)-1-methyl-5-pentafluoroethyl-1H-benzimidazole(hereinafter referred to as “the present compound 38”) was synthesizedin the same manner as in Production Example 25 except for using2-(3-ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl)-5-iodo-1-methyl-1H-benzimidazoleinstead of2-(3-ethylsulfanyl-pyridin-2-yl)-5-iodo-1-methyl-1H-benzimidazole.

The Present Compound 38

¹H-NMR (CDCl₃) δ: 8.72 (1H, d), 8.20 (1H, s), 7.91 (1H, d), 7.60 (1H,d), 7.55 (1H, d), 4.00 (3H, s), 3.01 (2H, q), 1.39 (3H, t).

Production Example 37, 38

2-(3-ethylsulfinyl-5-trifluoromethyl-pyridin-2-yl)-1-methyl-5-pentafluoroethyl-1H-benzimidazole(hereinafter referred to as “the present compound 39”) and2-(3-ethylsulfonyl-5-trifluoromethyl-pyridin-2-yl)-1-methyl-5-pentafluoroethyl-1H-benzimidazole(hereinafter referred to as “the present compound 40”) were synthesizedin the same manner as in Production Examples 2 and 3 except for using2-(3-ethylsulfanyl-5-trifluoromethyl-pyridin-2-yl)-1-methyl-5-pentafluoroethyl-1H-benzimidazoleinstead of2-(3-ethylsulfanylpyridin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine.

The Present Compound 39

¹H-NMR (CDCl₃) δ: 9.05 (1H, d), 8.91 (1H, d), 8.10 (1H, s), 7.66-7.60(2H, m), 4.33 (3H, s), 3.80-3.69 (1H, m), 3.17-3.07 (1H, m), 1.50 (3H,t).

The Present Compound 40

¹H-NMR (CDCl₃) δ: 9.22 (1H, d), 8.77 (1H, d), 8.08 (1H, s), 7.63 (1H,d), 7.58 (1H, d), 3.99 (2H, q), 3.84 (3H, s), 1.40 (3H, t).

Production Example 39 (1)

To a mixture of methyl-(2-nitro-4-trifluoromethyl-phenyl)-amine (16 g)and acetonitrile (200 ml) was added N-bromosuccinimide (15 g) whileice-cooling. The reaction mixture was stirred at room temperature for 5hours. To the resulting reaction mixture was poured saturated aqueoussodium hydrogen carbonate solution, and then the mixture was extractedwith ethyl acetate. The organic layer was dried over magnesium sulfate,and concentrated under reduced pressure. The residue was subjected tosilica gel column chromatography to give(2-bromo-6-nitro-4-trifluoromethyl-phenyl)-methyl-amine (15 g).

(2-bromo-6-nitro-4-trifluoromethyl-phenyl)-methyl-amine

¹H-NMR (CDCl₃) δ: 8.12 (1H, s), 7.86 (1H, s), 6.48 (1H, brs), 3.07 (3H,d).

Production Example 39 (2)

To a mixture of an iron powder (11 g), acetic acid (12 ml), THF (40 ml),and water (10 ml) was added dropwise a mixture of(2-bromo-6-nitro-4-trifluoromethyl-phenyl)-methyl-amine (10 g) and THF(50 ml) while stirring and heating at 70° C. After that, the mixture wasstirred at 70° C. for 3 hours. The resulting reaction mixture wasfiltered through celite (registered trademark), and washed with THF. Theresulting filtrate was concentrated under reduced pressure. To theresulting residue was poured 10% sodium hydroxide aqueous solution, andthe mixture was extracted with ethyl acetate. The organic layer wasdried over magnesium sulfate, and concentrated under reduced pressure togive 3-bromo-N²-methyl-5-trifluoromethyl-benzene-1,2-diamine (11 g).

3-bromo-N²-methyl-5-trifluoromethyl-benzene-1,2-diamine

Production Example 39 (3)

3-chloro-pyridin-2-carboxylic acid(3-bromo-2-methylamino-5-trifluoromethyl-phenyl)-amide (hereinafterreferred to as “intermediate compound (M20-43)”) was synthesized in thesame manner as in Production Example 9 (1) except for using3-bromo-N²-methyl-5-trifluoromethyl-benzene-1,2-diamine instead of5-iodo-N²-methyl-pyridin-2,3-diamine.

Intermediate Compound (M20-43)

¹H-NMR (CDCl₃) δ: 10.63 (1H, s), 8.77 (1H, d), 8.58 (1H, dd), 7.91 (1H,dd), 7.56 (1H, d), 7.47 (1H, dd), 3.75-3.68 (1H, m), 2.83 (3H, d).

Production Example 39 (4)

2-(3-ethylsulfanyl-pyridin-2-yl)-7-bromo-1-methyl-5-trifluoromethyl-1H-benzimidazole(hereinafter referred to as “the present compound 75”),3-ethylsulfanyl-pyridin-2-carboxylic acid(3-bromo-2-methylamino-5-trifluoromethyl-phenyl)-amide (hereinafterreferred to as “intermediate compound (M3-42)”) and2-(3-chloro-pyridin-2-yl)-7-bromo-1-methyl-5-trifluoromethyl-1H-benzimidazole(hereinafter referred to as “intermediate compound (M6-43)”) weresynthesized in the same manner as in Production Example 28 (2) exceptfor using the intermediate compound (M20-43) instead of the intermediatecompound (M20-29).

The Present Compound 75

¹H-NMR (CDCl₃) δ: 8.54 (1H, dd), 8.08 (1H, d), 7.79 (1H, dd), 7.72 (1H,d), 7.40 (1H, dd), 4.13 (3H, s), 2.94 (2H, q), 1.32 (3H, t).

Intermediate Compound (M3-42)

¹H-NMR (CDCl₃) δ: 10.80 (1H, s), 8.82 (1H, s), 8.38 (1H, dd), 7.74 (1H,d), 7.54 (1H, s), 7.42 (1H, dd), 3.75-3.65 (1H, brm), 2.97 (2H, q), 2.82(3H, d), 1.45 (3H, t).

Intermediate Compound (M6-43)

¹H-NMR (CDCl₃) δ: 8.71 (1H, dd), 8.08 (1H, d), 7.95 (1H, dd), 7.74 (1H,d), 7.47 (1H, dd), 4.09 (3H, s).

Production Example 40

2-(3-ethylsulfonyl-pyridin-2-yl)-7-bromo-1-methyl-5-trifluoromethyl-1H-benzimidazole(hereinafter referred to as “the present compound 46”) was synthesizedin the same manner as in Production Example 5 except for using2-(3-ethylsulfanyl-pyridin-2-yl)-7-bromo-1-methyl-5-trifluoromethyl-1H-benzimidazoleinstead of2-(3-ethylsulfanyl-5-trifluoromethylpyridin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine.

The Present Compound 46

¹H-NMR (CDCl₃) δ: 8.99 (1H, dd), 8.51 (1H, dd), 8.00 (1H, d), 7.75 (1H,d), 7.72 (1H, dd), 4.03 (3H, s), 3.73 (2H, q), 1.33 (3H, t).

Production Examples 41 and 42

A mixture of2-(3-ethylsulfanyl-5-trifluoromethylpyridin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine(1.0 g), m-chloroperbenzoic acid (purity: not less than 65%) (2.72 g)and chloroform (5 ml) was refluxed for 8 hours, and m-chloroperbenzoicacid (purity: not less than 65%) (2.0 g) was added thereto, and themixture was further refluxed for 5 hours. To the cooled reaction mixturewas poured aqueous 10% sodium thiosulfate solution, and the mixture wasextracted with chloroform. The organic layer was washed with saturatedaqueous sodium hydrogen carbonate solution, dried over anhydrousmagnesium sulfate, and concentrated under reduced pressure to give2-(3-ethylsulfonyl-5-trifluoromethylpyridin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine4-oxide (362 mg), which is hereinafter referred to as “the presentcompound 47”), and2-(3-ethylsulfonyl-1-oxy-5-trifluoromethylpyridin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine(45 mg), which is hereinafter referred to as “the present compound 51”.

The Present Compound 47

¹H-NMR (CDCl₃) δ: 9.27 (1H, d), 8.76 (1H, d), 8.49 (1H, d), 7.94 (1H,d), 4.33 (3H, s), 3.80 (2H, q), 1.40 (3H, t).

The Present Compound 51

¹H-NMR (CDCl₃) δ: 8.75 (1H, s), 8.50 (1H, s), 8.12 (1H, s), 7.94 (1H,s), 4.28 (3H, s), 3.75-3.65 (1H, m), 3.55-3.44 (1H, m), 1.38 (3H, t).

Production Example 43 (1)

A mixture of 2-chloro-3-nitro-5-trifluoromethylpyridine (2.60 g),2,2,2-trifluoroethylamine (0.79 g), N,N-diisopropylethylamine (1.04 g)and N-methyl-2-pyrrolidone (5 ml) was stirred at room temperature for 10hours. To the reaction mixture was poured aqueous 10% citric acidsolution, and then the mixture was extracted with ethyl acetate. Theorganic layer was washed with water, dried over sodium sulfate, andconcentrated under reduced pressure to give(3-nitro-5-trifluoromethylpyridin-2-yl)-(2,2,2-trifluoroethyl)amine(1.83 g).

(3-nitro-5-trifluoromethylpyridin-2-yl)-(2,2,2-trifluoroethyl)amine

¹H-NMR (CDCl₃) δ: 8.72 (1H, d), 8.68 (1H, d), 8.59 (1H, brs), 4.54-4.41(2H, m).

Production Example 43 (2)

A mixture of an iron powder (2.12 g), ethanol 6 ml), water 4 ml) andacetic acid 0.1 ml) was added dropwise a mixture of(3-nitro-5-trifluoromethylpyridin-2-yl)-(2,2,2-trifluoroethyl)amine(1.83 g) and ethanol (10 ml) at 70° C., and then the mixture was stirredat 70° C. for 1 hour. After allowing to cool, the cooled reactionmixture was filtrated. To the filtrate was added water, and then themixture was extracted with ethyl acetate. The organic layer was washedwith water, dried over sodium sulfate, and concentrated under reducedpressure to giveN²-(2,2,2-trifluoroethyl)-5-trifluoromethylpyridin-2,3-diamine (1.59 g).

N²-(2,2,2-trifluoroethyl)-5-trifluoromethylpyridin-2,3-diamine

¹H-NMR (CDCl₃) δ: 8.04-8.02 (1H, m), 7.10-7.07 (1H, m), 4.81 (1H, brs),4.31-4.20 (2H, m), 3.34 (2H, brs).

Production Example 43 (3)

A mixture ofN²-(2,2,2-trifluoroethyl)-5-trifluoromethylpyridin-2,3-diamine (0.52 g),3-ethylsulfanylpyridin-2-carboxylic acid (0.37 g), WSC (0.46 g), HOBt(27 mg) and pyridine (2 ml) was stirred at room temperature for 3 hours.To the reaction mixture was poured aqueous 10% citric acid solution, andthen the mixture was extracted with ethyl acetate. The organic layer waswashed with water, dried over sodium sulfate, and concentrated underreduced pressure to give 3-ethylsulfanyl pyridin-2-carboxylic acid[2-(2,2,2-trifluoroethyl)amino-5-trifluoromethylpyridin-3-yl]amide (0.75g), which is hereinafter referred to as “intermediate compound (M3-43)”.

Intermediate Compound (M3-43)

Production Example 43 (4)

A mixture of the intermediate compound (M3-43) (0.75 g) and acetic acid(5 ml) was stirred while heating under reflux for 2 days. After coolingto room temperature, the mixture was concentrated under reducedpressure. The crude product was subjected to silica gel columnchromatography to give2-(3-ethylsulfanylpyridin-2-yl)-3-(2,2,2-trifluoroethyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine(0.53 g), which is hereinafter referred to as “the present compound 65”.

The Present Compound 65

¹H-NMR (CDCl₃) δ: 8.77-8.74 (1H, m), 8.48 (1H, dd), 8.45-8.42 (1H, m),7.82 (1H, dd), 7.40 (1H, dd), 5.64 (2H, q), 2.99 (2H, q), 1.35 (3H, t).

Production Example 44 (1)

A mixture ofN²-(2,2,2-trifluoroethyl)-5-trifluoromethylpyridin-2,3-diamine (0.52 g),3-ethylsulfanyl-5-trifluoromethylpyridin-2-carboxylic acid (0.50 g), WSC(0.46 g), HOBt (27 mg) and pyridine (2 ml) was stirred at roomtemperature for 3 hours. To the reaction mixture was poured aqueous 10%citric acid solution, and then the mixture was extracted with ethylacetate. The organic layer was washed with water, dried over sodiumsulfate, and concentrated under reduced pressure to give3-ethylsulfanyl-5-trifluoromethylpyridin-2-carboxylic acid[2-(2,2,2-trifluoroethyl)amino-5-trifluoromethylpyridin-3-yl]amide (0.89g), which is hereinafter referred to as “intermediate compound (M3-44)”.

Intermediate Compound (M3-44)

Production Example 44 (2)

A mixture of the intermediate compound (M3-44) (0.89 g),p-toluenesulfonic acid monohydrate (1.14 g), N-methyl-2-pyrrolidone (10ml) and xylene (10 ml) was heated under reflux while dehydrating withthe Dean-Stark apparatus for 8 hours, and then the reaction mixture wasallowed to cool. To the cooled reaction mixture was added water, and themixture was extracted with ethyl acetate. The organic layer was washedwith water, dried over sodium sulfate, and concentrated under reducedpressure. The crude product was subjected to silica gel columnchromatography to give2-(3-ethylsulfanyl-5-trifluoromethylpyridin-2-yl)-3-(2,2,2-trifluoroethyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine(0.76 g), which is hereinafter referred to as “the present compound 66”.

The Present Compound 66

¹H-NMR (CDCl₃) δ: 8.80 (1H, d), 8.70 (1H, d), 8.48 (1H, d), 7.96 (1H,d), 5.67 (2H, q), 3.04 (2H, q), 1.40 (3H, t).

Production Example 45

To a mixture of the present compound 65 (0.32 g) and chloroform (2 ml)was added m-chloroperbenzoic acid (purity: not less than 65%) (0.36 g)while ice-cooling. The mixture was heated to room temperature, andstirred 1 hour. To the mixture were added saturated aqueous sodiumhydrogen carbonate solution and saturated aqueous sodium thiosulfatesolution, and then the mixture was extracted with chloroform. Theorganic layer was washed with water, dried over sodium sulfate, andconcentrated under reduced pressure. The crude product was subjected tosilica gel column chromatography to give2-(3-ethylsulfonylpyridin-2-yl)-3-(2,2,2-trifluoroethyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine(0.32 g), which is hereinafter referred to as “the present compound 67”.

The Present Compound 67

¹H-NMR (CDCl₃) δ: 8.98 (1H, dd), 8.80 (1H, d), 8.59 (1H, dd), 8.37 (1H,d), 7.75 (1H, dd), 5.31 (2H, q), 3.95 (2H, q), 1.40 (3H, t).

Production Example 46

To a mixture of the present compound 66 (0.32 g) and chloroform (2 ml)was added m-chloroperbenzoic acid (purity: not less than 65%) (0.31 g)while ice-cooling. The mixture was heated to room temperature, andstirred for 1 hour. To the mixture were poured saturated aqueous sodiumhydrogen carbonate solution and saturated aqueous sodium thiosulfatesolution, and the mixture was extracted with chloroform. The organiclayer was washed with water, dried over sodium sulfate, and concentratedunder reduced pressure. The resulting crude product was washed withhexane to give2-(3-ethylsulfonyl-5-trifluoromethylpyridin-2-yl)-3-(2,2,2-trifluoroethyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine(0.28 g), which is hereinafter referred to as “the present compound 68”.

The Present Compound 68

¹H-NMR (CDCl₃) δ: 9.22 (1H, d), 8.83-8.83 (2H, m), 8.40 (1H, d), 5.36(2H, q), 4.05 (2H, q), 1.45 (3H, t).

Production Example 47 (1)

A mixture of 2-chloro-5-iodopyridine (20.0 g), sodiumpentafluoropropionate (77.8 g), copper (I) iodide (31.8 g), xylene (84ml) and N-methyl pyrrolidone (84 ml) was heated to 160° C., and stirredwhile heating under reflux 6 hours. The reaction mixture was cooled toroom temperature, and water was poured thereto. Then, the mixture wasextracted with methyl-tert-butyl ether. The organic layer was dried oversodium sulfate, and concentrated under reduced pressure to give2-chloro-5-pentafluoroethyl pyridine.

2-chloro-5-pentafluoroethyl pyridine

¹H-NMR (CDCl₃) δ: 8.65-8.62 (1H, m), 7.85-7.81 (1H, m), 7.48-7.44 (1H,m)

Production Example 47 (2)

A mixture of the half amount of 2-chloro-5-pentafluoroethyl pyridineobtained in Production Example 47 (1), zinc (II) cyanide (14.4 g),tetrakistriphenylphosphine palladium (2.42 g) and N-methyl pyrrolidone(84 ml) was heated to 80° C., and stirred for 2.5 hours. The reactionmixture was cooled to room temperature, and water and methyl-tert-butylether were poured thereto. The resulting precipitate was filtratedthrough celite (registered trademark), and the residue was washed withmethyl-tert-butyl ether. The filtrate was extracted withmethyl-tert-butyl ether. The organic layer was dried over sodiumsulfate, and concentrated under reduced pressure.

The crude product was subjected to silica gel column chromatography togive 2-cyano-5-pentafluoroethyl pyridine (4.19 g).

2-cyano-5-pentafluoroethyl pyridine

¹H-NMR (CDCl₃) δ: 8.97-8.96 (1H, m), 8.12-8.09 (1H, m), 7.90-7.87 (1H,m)

Production Example 47 (3)

A mixture of water (17 ml) and concentrated sulfuric acid (17 ml) washeated to 100° C., and thereto was added dropwise2-cyano-5-pentafluoroethyl pyridine (3.81 g) while heating. Then, themixture was stirred at 100° C. for 2.5 hours. After cooling to roomtemperature, the reaction mixture was poured to ice water. Theprecipitated solid was filtrated and washed with water. The resultingsolid was dried under reduced pressure to give5-pentafluoropyridin-2-carboxylic acid (3.52 g).

5-pentafluoropyridin-2-carboxylic acid

¹H-NMR (CDCl₃) δ: 8.92-8.88 (1H, m), 8.44-8.39 (1H, m), 8.25-8.20 (1H,m)

Production Example 47 (4)

A mixture of tetramethyl piperidine (5.5 ml) and THF (58 ml) was cooledto −78° C., and thereto was added dropwise a solution of 1.6M n-butyllithium in hexane. After heating to room temperature, the mixture wasstirred for 10 minutes. The mixture was cooled to −78° C. again, andthereto was added dropwise a solution of5-pentafluoropyridin-2-carboxylic acid (3.52 g) in THF. Then, themixture was stirred at −78° C. for 1 hour, and thereto was addeddropwise diethyl disulfide (4.0 ml) at −78°. After heating to roomtemperature, the mixture was stirred for 1 hour. To the reaction mixturewas poured 1N hydrochloric acid, followed by a 5N aqueous sodiumhydroxide solution. Then, the aqueous layer was washed withmethyl-tert-butyl ether, and thereto was poured 12N hydrochloric acid.The precipitated solid was filtrated, and dissolved in methyl-tert-butylether. The solid was dried over sodium sulfate, and concentrated underreduced pressure to give 3-ethylsulfanyl-5-pentafluoroethylpyridin-2-carboxylic acid (1.99 g), which is hereinafter referred to as“intermediate compound (M2-7)”.

Intermediate Compound (M2-7)

¹H-NMR (CDCl₃) b: 8.51-8.50 (1H, m), 7.89-7.87 (1H, m), 3.01 (2H, q),1.46 (3H, t)

Production Example 47 (5)

A mixture of N²-methyl-5-trifluoromethylpyridin-2,3-diamine (0.50 g),the intermediate compound (M2-7) (0.79 g), WSC (0.37 g), HOBt (35 mg)and pyridine (5 ml) was stirred at room temperature for 3 hours. To thereaction mixture was poured water, and then the mixture was extractedwith methyl-tert-butyl ether. The organic layer was dried over magnesiumsulfate and concentrated under reduced pressure to give3-ethylsulfanyl-5-pentafluoroethyl pyridin-2-carboxylic acid(2-methylamino-5-trifluoromethylpyridin-3-yl)amide, which is hereinafterreferred to as “intermediate compound (M3-45)”.

Intermediate Compound (M3-45)

¹H-NMR (CDCl₃) δ: 9.57 (1H, brs), 8.54-8.52 (1H, m), 8.37-8.35 (1H, m),7.94-7.92 (1H, m), 7.89-7.87 (1H, m), 4.97 (1H, brs), 3.08 (3H, d), 2.99(2H, q), 1.45 (3H, t)

A mixture of the total amount of the resulting intermediate compound(M3-45) and acetic acid (5 ml) was heated to 120° C., and stirred whileheating under reflux for 3 hours. After cooling to room temperature, themixture was concentrated under reduced pressure. The crude product wassubjected to silica gel column chromatography to give2-(3-ethylsulfanyl-5-pentafluoroethylpyridin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine(0.77 g), which is hereinafter referred to as “the present compound 71”.

The Present Compound 71

¹H-NMR (CDCl₃) δ: 8.78-8.76 (1H, m), 8.71-8.69 (1H, m), 8.44-8.42 (1H,m), 7.91-7.89 (1H, m), 4.13 (3H, s), 3.02 (2H, q), 1.39 (3H, t)

Production Example 48

To a mixture of the present compound 71 (0.47 g) and chloroform (10 ml)was added m-chloroperbenzoic acid (purity: not less than 65%) (0.57 g)while ice-cooling. Then, the mixture was heated to room temperature, andstirred for 1 hour. To the mixture were poured saturated aqueous sodiumhydrogen carbonate solution and saturated aqueous sodium thiosulfatesolution, and then the mixture was extracted with chloroform. Theorganic layer was dried over sodium sulfate, and concentrated underreduced pressure. The crude product was subjected to silica gel columnchromatography to give2-(3-ethylsulfonyl-5-pentafluoroethylpyridin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine(0.39 g), which is hereinafter referred to as “the present compound 72”.

The Present Compound 72

¹H-NMR (CDCl₃) δ: 9.21-9.19 (1H, m), 8.81-8.79 (1H, m), 8.76-8.75 (1H,m), 8.35-8.33 (1H, m), 3.99-3.93 (5H, m), 1.41 (3H, t)

Production Example 49

A mixture of N²-methyl-5-pentafluoroethylpyridin-2,3-diamine (0.50 g),the intermediate compound (M2-7) (0.62 g), WSC (0.29 g), HOBt (28 mg)and pyridine (0.4 ml) was stirred at room temperature for 3 hours. Tothe reaction mixture was poured water, and the mixture was extractedwith methyl-tert-butyl ether. The organic layer was dried over magnesiumsulfate and concentrated under reduced pressure to give3-ethylsulfanyl-5-pentafluoroethylpyridin-2-carboxylic acid(2-methylamino-5-pentafluoroethyl pyridin-3-yl)amide, which ishereinafter referred to as “intermediate compound (M3-46)”.

Intermediate Compound (M3-46)

¹H-NMR (CDCl₃) δ: 9.59 (1H, brs), 8.54-8.52 (1H, m), 8.32-8.30 (1H, m),7.89-7.87 (1H, m), 7.85-7.83 (1H, m), 5.04 (1H, brs), 3.09 (3H, d), 2.99(2H, q), 1.45 (3H, t)

A mixture of the total amount of the resulting intermediate compound(M3-46) and acetic acid (4 ml) was heated to 120° C., and stirred whileheating under reflux for 3 hours. After cooling to room temperature, themixture was concentrated under reduced pressure. The crude product wassubjected to silica gel column chromatography to give2-(3-ethylsulfanyl-5-pentafluoroethylpyridin-2-yl)-3-methyl-6-pentafluoroethyl-3H-imidazo[4,5-b]pyridine(0.84 g), which is hereinafter referred to as “the present compound 73”.

The Present Compound 73

¹H-NMR (CDCl₃) δ: 8.72-8.69 (2H, m), 8.42-8.41 (1H, m), 7.90-7.89 (1H,m), 4.15-4.12 (3H, m), 3.02 (2H, q), 1.40 (3H, t)

Production Example 50

To the mixture of the present compound 73 (0.54 g) and chloroform (11ml) was added m-chloroperbenzoic acid (purity: not less than 65%) (0.59g) while ice-cooling. The mixture was heated to room temperature, andstirred for 1 hour. To the mixture were poured saturated aqueous sodiumhydrogen carbonate solution and saturated aqueous sodium thiosulfatesolution, and then the mixture was extracted with chloroform. Theorganic layer was dried over sodium sulfate, and concentrated underreduced pressure. The crude product was subjected to silica gel columnchromatography to give 2-(3-ethylsulfonyl-5-pentafluoroethylpyridin-2-yl)-3-methyl-6-pentafluoroethyl-3H-imidazo[4,5-b]pyridine(0.34 g), which is hereinafter referred to as “the present compound 74”.

The Present Compound 74

¹H-NMR (CDCl₃) δ: 9.21-9.20 (1H, m), 8.77-8.74 (2H, m), 8.32-8.31 (1H,m), 4.00-3.94 (5H, m), 1.41 (3H, t)

The compounds as described in Production Examples and the compoundsproduced in the same manner as in Production Examples are shown below.

A compound represented by the formula (1):

wherein R¹, R², R³, R⁴, R⁵, R⁶, A¹, A², A³ and n are any of thecombinations as listed in [Table 36] to [Table 58].

TABLE 36 The present compound R¹ R² R³ R⁴ R⁵ R⁶ A¹ A² A³ n  1 Et H H HCF₃ H NMe CH N 0  2 Et H H H CF₃ H NMe CH N 1  3 Et H H H CF₃ H NMe CH N2  4 Et H CF₃ H CF₃ H NMe CH N 0  5 Et H CF₃ H CF₃ H NMe CH N 2  6 Et HH H CF₂CF₃ H NMe CH N 0  7 Et H H H CF₂CF₃ H NMe CH N 1  8 Et H H HCF₂CF₃ H NMe CH N 2  9 Et H H H I H NMe CH N 0 10 Et H CF₃ H CF₃ H S CHN 0 11 Et H CF₃ H CF₃ H S CH N 2 12 Et H H H CF₃ H S CH N 2 13 Et H H HSCF₃ H NMe CH N 0 14 Et H H H SCF₃ H NMe CH N 1 15 Et H H H SCF₃ H NMeCH N 2 16 Et H H H SO₂CF₃ H NMe CH N 2 17 Et H CF₃ H CF₂CF₃ H NMe CH N 018 Et H CF₃ H CF₂CF₃ H NMe CH N 1 19 Et H CF₃ H CF₂CF₃ H NMe CH N 2 20Et H H H SOCF₃ H NMe CH N 2 21 Et H H H I H NMe CH CH 0  22* Et H H HCF₃ H S CH N 2 23 Et H H H SF₅ H NMe CH CH 0 24 Et H H H SF₅ H NMe CH CH2 25 Et H CF₃ H SO₂CF₃ H NMe CH N 2

TABLE 37 The present compound R¹ R² R³ R⁴ R⁵ R⁶ A¹ A² A³ n 26 Et H H HCF₂CF₃ H NMe CH CH 0 27 Et H H H CF₂CF₃ H NMe CH CH 2 28 Et H CF₃ H SCF₃H NMe CH N 0 29 Et H CF₃ H SCF₃ H NMe CH N 1 30 Et H H H CF₃ H NMe CH CH0 31 Et H H H CF₃ H NMe CH CH 1 32 Et H H H CF₃ H NMe CH CH 2 33 Et HCF₃ H CF₃ H NMe CH CH 0 34 Et H CF₃ H CF₃ H NMe CH CH 1 35 Et H CF₃ HCF₃ H NMe CH CH 2  36* Et H H H CF₃ H NMe CH N 2  37* Et H H H CF₃ H NMeCH N 2 38 Et H CF₃ H CF₂CF₃ H NMe CH CH 0 39 Et H CF₃ H CF₂CF₃ H NMe CHCH 1 40 Et H CF₃ H CF₂CF₃ H NMe CH CH 2 41 Et H H H CF₃ H S CH N 0 42 EtH CF₃ H I H NMe CH N 0 43 Et H CF₃ H SH H NMe CH N 0 44 Et H CF₃ H SCF₃H NMe CH N 2 45 Et H CF₃ H I H NMe CH CH 0 46 Et H H H CF₃ H NMe CH CBr2  47* Et H H H CF₂CF₃ H NMe CH CH 2  48* Et H CF₃ H CF₃ H NMe CH N 2 49Et H H H OCF₃ H NMe CH CH 0 50 Et H H H OCF₃ H NMe CH CH 2

TABLE 38 The present compound R¹ R² R³ R⁴ R⁵ R⁶ A¹ A² A³ n  51* Et H CF₃H CF₃ H NMe CH N 2 52 Et H H H CF₃ H S CH CH 0 53 Et H H H CF₃ H S CH CH2 54 Et H CF₃ H CF₃ H S CH CH 0 55 Et H CF₃ H CF₃ H S CH CH 2 56 Et H HH CF₃ OMe NMe CH CH 2 57 Et H H H C(OH)₂CF₃ H NMe CH N 0 58 Et H H HC(OH)₂CF₃ H NMe CH N 2 59 Et H CF₃ H CO₂Me H NMe CH N 0 60 Et H CF₃ HSOCF₃ H NMe CH N 2 61 Et H H H SCF₃ H NMe CH CH 0 62 Et H H H SCF₃ H NMeCH CH 1 63 Et H H H SCF₃ H NMe CH CH 2 64 Et H H H SO₂CF₃ H NMe CH CH 265 Et H H H CF₃ H NCH₂CF₃ CH N 0 66 Et H CF₃ H CF₃ H NCH₂CF₃ CH N 0 67Et H H H CF₃ H NCH₂CF₃ CH N 2 68 Et H CF₃ H CF₃ H NCH₂CF₃ CH N 2 69 Et HCF₃ H CO₂Me H NMe CH N 2  70* Et H CF₃ H CO₂Me H NMe CH N 2 71 Et HCF₂CF₃ H CF₃ H NMe CH N 0 72 Et H CF₂CF₃ H CF₃ H NMe CH N 2 73 Et HCF₂CF₃ H CF₂CF₃ H NMe CH N 0 74 Et H CF₂CF₃ H CF₂CF₃ H NMe CH N 2 75 EtH H H CF₃ H NMe CH CBr 0

TABLE 39 The present compound R¹ R² R³ R⁴ R⁵ R⁶ A¹ A² A³ n 76 Et H H HCF₃ H NH CH N 0 77 Et H H H CF₃ H NH CH N 2 78 Et H CF₃ H CF₃ H NH CH N0 79 Et H CF₃ H CF₃ H NH CH N 2 80 Et H H H CF₃ H O CH N 0 81 Et H H HCF₃ H O CH N 2 82 Et H CF₃ H CF₃ H O CH N 0 83 Et H CF₃ H CF₃ H O CH N 284 Et H H H CF₃ H O CH CH 0 85 Et H H H CF₃ H O CH CH 2 86 Et H CF₃ HCF₃ H O CH CH 0 87 Et H CF₃ H CF₃ H O CH CH 2 88 Et H H H CF₃ Cl NMe CHN 2 89 Et H CF₃ H CF₃ Cl NMe CH N 2 90 Et H H H CF₃ SEt NMe CH N 2 91 EtH CF₃ H CF₃ SEt NMe CH N 2 92 Et H H H CF₃ OH NMe CH N 2 93 Et H CF₃ HCF₃ OH NMe CH N 2 94 Et H H H CF₃ OMe NMe CH N 2 95 Et H CF₃ H CF₃ OMeNMe CH N 2 96 Et H H H CF₃ SMe NMe CH N 2 97 Et H CF₃ H CF₃ SMe NMe CH N2 98 Et H H H CF₃ NMe₂ NMe CH N 2 99 Et H CF₃ H CF₃ NMe₂ NMe CH N 2 100Et H H H CF₃ Ph NMe CH N 2

TABLE 40 The present compound R¹ R² R³ R⁴ R⁵ R⁶ A¹ A² A³ n 101 Et H CF₃H CF₃ Ph NMe CH N 2 102 CH₂CycPr H H H CF₃ H NMe CH N 2 103 CH₂CycPr HCF₃ H CF₃ H NMe CH N 2 104 CF₃ H H H CF₃ H NMe CH N 2 105 CF₃ H CF₃ HCF₃ H NMe CH N 2 106 CH₂CF₃ H H H CF₃ H NMe CH N 2 107 CH₂CF₃ H CF₃ HCF₃ H NMe CH N 2 108 Et Cl H H CF₃ H NMe CH N 2 109 Et H Cl H CF₃ H NMeCH N 2 110 Et H H Cl CF₃ H NMe CH N 2 111 Et H 2-pyridyl H CF₃ H NMe CHN 2 112 Et H 2- H CF₃ H NMe CH N 2 pyrimidinyl 113 Et H 3-chloro- H CF₃H NMe CH N 2 2-pyridyl 114 Et H 3-chloro- H CF₃ H NMe CH N 2 5-trifluoromethyl- 2- pyridyl 115 Et H OCF₃ H CF₃ H NMe CH N 2 116 Et HSCF₃ H CF₃ H NMe CH N 2 117 Et H SOCF₃ H CF₃ H NMe CH N 2 118 Et HSO₂CF₃ H CF₃ H NMe CH N 2 119 Et H CF(CF₃)₂CF₃ H CF₃ H NMe CH N 2 120 EtH CF₂CF₂CF₃ H CF₃ H NMe CH N 2 121 Et H Br H CF₃ H NMe CH N 2 122 Et H IH CF₃ H NMe CH N 2 123 Et H Me H CF₃ H NMe CH N 2 124 Et H OMe H CF₃ HNMe CH N 2 125 Et H H H CF(CF₃)₂ H NMe CH N 2

TABLE 41 The present compound R¹ R² R³ R⁴ R⁵ R⁶ A¹ A² A³ n 126 Et H CF₃H CF(CF₃)₂ H NMe CH N 2 127 Et H CF₃ H SF₅ H NMe CH N 2 128 Et H H HCF₂CF₂CF₃ H NMe CH N 2 129 Et H CF₃ H CF₂CF₂CF₃ H NMe CH N 2 130 Et H HH SCF₂CF₃ H NMe CH N 2 131 Et H CF₃ H SCF₂CF₃ H NMe CH N 2 132 Et H H HSO₂CF₂CF₃ H NMe CH N 2 133 Et H CF₃ H SO₂CF₂CF₃ H NMe CH N 2 134 Et H HH CF₃ H NCH₂OMe CH N 2 135 Et H CF₃ H CF₃ H NCH₂OMe CH N 2 136 Et H H HCF₃ H NCH₂C≡CH CH N 2 137 Et H CF₃ H CF₃ H NCH₂C≡CH CH N 2 138 Et H H HCF₃ H NMe CH CCN 2 139 Et H CF₃ H CF₃ H NMe CH CCN 2 140 Et H H H CF₃ HNMe CH CF 2 141 Et H CF₃ H CF₃ H NMe CH CF 2 142 Et H H H CF₃ H NMe CHCMe 2 143 Et H CF₃ H CF₃ H NMe CH CMe 2 144 Et H H H CF₃ H NMe CH COMe 2145 Et H CF₃ H CF₃ H NMe CH COMe 2 146 Et H H H CF₃ H NMe CH CSCH₂CH₃ 2147 Et H CF₃ H CF₃ H NMe CH CSCH₂CH₃ 2 148 Et H H H CF₃ H NMe CHCSO₂CH₂CH₃ 2 149 Et H CF₃ H CF₃ H NMe CH CSO₂CH₂CH₃ 2 150 Me H H H CF₃ HNMe CH N 0

TABLE 42 The present compound R¹ R² R³ R⁴ R⁵ R⁶ A¹ A² A³ n 151 Me H H HCF₃ H NMe CH N 1 152 Me H H H CF₃ H NMe CH N 2 153 Pr H H H CF₃ H NMe CHN 0 154 Pr H H H CF₃ H NMe CH N 1 155 Pr H H H CF₃ H NMe CH N 2 156CH₂CH═CH₂ H H H CF₃ H NMe CH N 0 157 CH₂CH═CH₂ H H H CF₃ H NMe CH N 2158 iPr H H H CF₃ H NMe CH N 0 159 iPr H H H CF₃ H NMe CH N 1 160 iPr HH H CF₃ H NMe CH N 2 161 tBu H H H CF₃ H NMe CH N 0 162 tBu H H H CF₃ HNMe CH N 1 163 tBu H H H CF₃ H NMe CH N 2 164 CF₃ H H H CF₃ H NMe CH N 0165 CF₃ H H H CF₃ H NMe CH N 1 166 Et H H H CF₃ H NEt CH N 0 167 Et H HH CF₃ H NEt CH N 1 168 Et H H H CF₃ H NEt CH N 2 169 Et H H H CF₃ H NPrCH N 0 170 Et H H H CF₃ H NPr CH N 1 171 Et H H H CF₃ H NPr CH N 2 172Et H H H CF₃ H NiPr CH N 0 173 Et H H H CF₃ H NiPr CH N 1 174 Et H H HCF₃ H NiPr CH N 2 175 Et H H H CF₃ H NCycPr CH N 0

TABLE 43 The present com- pound R¹ R² R³ R⁴ R⁵ R⁶ A¹ A² A³ n 176 Et H HH CF₃ H NCycPr CH N 1 177 Et H H H CF₃ H NCycPr CH N 2 178 Et H H H CF₃H NCH₂OEt CH N 0 179 Et H H H H CF₃ NCH₂OEt N CH 0 180 Et H H H CF₃ HNCH₂OEt CH N 1 181 Et H H H CF₃ H NCH₂OEt CH N 2 182 Et H H H CF₃ HNCH₂OMe CH N 0 183 Et H H H Me H NMe CH N 0 184 Et H H H Me H NMe CH N 1185 Et H H H Me H NMe CH N 2 186 Et H H H Br H NMe CH N 0 187 Et H H HBr H NMe CH N 1 188 Et H H H Br H NMe CH N 2 189 Et H H H I H NMe CH N 1190 Et H H H I H NMe CH N 2 191 Et H H H CN H NMe CH N 0 192 Et H H H CNH NMe CH N 1 193 Et H H H CN H NMe CH N 2 194 Et H H H CHO H NMe CH N 0195 Et H H H CF₂H H NMe CH N 0 196 Et H H H CF₂H H NMe CH N 1 197 Et H HH CF₂H H NMe CH N 2 198 Et H H H Ph H NMe CH N 0 199 Et H H H Ph H NMeCH N 2 200 Et H H H 2- H NMe CH N 0 fluoro- phenyl

TABLE 44 The present compound R¹ R² R³ R⁴ R⁵ R⁶ A¹ A² A³ n 201 Et H H H2-fluoro- H NMe CH N 1 phenyl 202 Et H H H 2-fluoro- H NMe CH N 2 phenyl203 Et H H H 3-fluoro- H NMe CH N 0 phenyl 204 Et H H H 3-fluoro- H NMeCH N 1 phenyl 205 Et H H H 3-fluoro- H NMe CH N 2 phenyl 206 Et H H H4-fluoro- H NMe CH N 0 phenyl 207 Et H H H 4-fluoro- H NMe CH N 2 phenyl208 Et H H H H CF₃ NMe N CH 0 209 Me H H H CF₃ H NMe CH CH 0 210 Et H HH CF₃ H NMe CH CCl 0 211 Et H H H CF₃ H NMe CH CCl 1 212 Et H H H CF₃ HNMe CH CCl 2 213 Et H H H CF₃ H NMe CH CBr 1 214 Me H H H CF₃ H O CH CH0 215 Et H H H CF₃ H O CH CH 1 216 Et H H H CF₃ H O CH N 1 217 Me H H HCF₃ H S CH CH 0 218 Et H H H CF₃ H S CH CH 1 219 Et Cl H H CF₃ H NMe CHN 0 220 Et Cl H H CF₃ H NMe CH N 1 221 Et H H H COCF₃ H NMe CH N 0 222Et H H H Cl H NMe CH N 0 223 Et H H H Cl H NMe CH N 1 224 Et H H H Cl HNMe CH N 2 225 Et H H H Br H NMe CCHO N 0

TABLE 45 The present compound R¹ R² R³ R⁴ R⁵ R⁶ A¹ A² A³ n 226 Et H HSEt CF₃ H NMe CH N 0 227 Et H H H CF₃ H NCH₂OEt CH CH 0 228 Et H H H HCF₃ NCH₂OEt N CH 0 229 Et H H H CF₃ H NCH₂CO₂Me CH N 0 230 Et H H H CF₃H NCH₂CO₂Et CH N 0 231 Et H H H CF₃ H N(CH₂)₂OMe CH N 0 232 Et H H H CF₃H NCH₂SMe CH N 0 233 Et H H H CF₃ H N(CH₂)₂SMe CH N 0 234 Et H H H CF₃ HNBu CH N 0 235 Et H H H CF₃ H NCO₂tBu CH N 0 236 Et H H H CH(OH)CF₃ HNMe CH N 0 237 Et H H H CHFCF₃ H NMe CH N 0 238 Et H F H CF₃ H NMe CH N0 239 Et H F H CF₃ H NMe CH N 1 240 Et H F H CF₃ H NMe CH N 2 241 Et OMeH H CF₃ H NMe CH N 0 242 Et OMe H H CF₃ H NMe CH N 1 243 Et H OMe H CF₃H NMe CH N 0 244 Et H OMe H CF₃ H NMe CH N 1 245 Et H OH H CF₃ H NMe CHN 0 246 Et H H H NH₂ H NMe CH N 0 247 Et H H H CHFCF₃ H NMe CH N 1 248Et H H H CHFCF₃ H NMe CH N 2 249 Et H H H CF₂CF₂CF₃ H NMe CH N 0 250 EtH H H CF₂CF₂CF₃ H NMe CH N 1

TABLE 46 The present compound R¹ R² R³ R⁴ R⁵ R⁶ A¹ A² A³ n 251 Et Cl H HCF₂CF₃ H NMe CH N 1 252 Et Cl H H CF₂CF₃ H NMe CH N 2 253 Et H Cl H CF₃H NMe CH N 0 254 Et H Cl H CF₃ H NMe CH N 1 255 Et H Cl H CF₂CF₃ H NMeCH N 1 256 Et H H Cl CF₃ H NMe CH N 0 257 Et H H Cl CF₃ H NMe CH N 1 258Et H H OMe CF₃ H NMe CH N 0 259 Et H H OMe CF₃ H NMe CH N 1 260 Et H HOMe CF₃ H NMe CH N 2 261 Et H H H SH H NMe CH N 0 262 Et H H H Et H NMeCH N 0 263 Et H H H iPr H NMe CH N 0 264 Et H H H NHEt H NMe CH N 0 265Et H H H NEt₂ H NMe CH N 0 266 Et H H H tBu H NMe CH N 0 267 Et H H H HCF₃ NMe CH N 0 268 Et F H H CF₃ H NMe CH N 0 269 Et F H H CF₃ H NMe CH N1 270 Et F H H CF₃ H NMe CH N 2 271 Et H H H H CF₃ NMe CH N 1 272 Et H HH H CF₃ NMe CH N 2 273 Et H H H NMe₂ H NMe CH N 0 274 Et H H Hpyrrolidin- H NMe CH N 0 1-yl 275 Et H H H NHCOMe H NMe CH N 0

TABLE 47 The present compound R¹ R² R³ R⁴ R⁵ R⁶ A¹ A² A³ n 276 Et H H HCH₂CF₃ H NMe CH N 0 277 Et H H H CF₃ H NMe N CH 0 278 Et H H H CF₃ H NMeN CH 1 279 Et H H H CF₃ H NMe N CH 2 280 Et H H H NMeCOMe H NMe CH N 0281 Et H H H NH₂ H NMe CH N 1 282 Et H CF₃ H CF₃ H NMe CH N 1 283 Et H HH NHCOCF₃ H NMe CH N 0 284 Et H H H NHCOCF₃ H NMe CH N 1 285 Et H H HNHCOCF₃ H NMe CH N 2 286 Et H H H 2-CF₃—Ph H NMe CH N 0 287 Et H H H3-CF₃—Ph H NMe CH N 0 288 Et H H H 4-CF₃—Ph H NMe CH N 0 289 Et H H HCF₃ H S CH N 1 290 CH₂CF₃ H H H CF₃ H NMe CH N 0 291 CH₂CF₃ H H H CF₃ HNMe CH N 1 292 Et Me H H CF₃ H NMe CH N 0 293 Et Me H H CF₃ H NMe CH N 1294 Et Me H H CF₃ H NMe CH N 2 295 Et H Me H CF₃ H NMe CH N 0 296 Et HMe H CF₃ H NMe CH N 1 297 Et H H H 2-CF₃—Ph H NMe CH N 1 298 Et H H H2-CF₃—Ph H NMe CH N 2 299 Et H H H 3-CF₃—Ph H NMe CH N 1 300 Et H H H3-CF₃—Ph H NMe CH N 2

TABLE 48 The present compound R¹ R² R³ R⁴ R⁵ R⁶ A¹ A² A³ n 301 Et H H H4-CF₃—Ph H NMe CH N 1 302 Et H H H 4-CF₃—Ph H NMe CH N 2 303 Et H H CF₃CF₃ H NMe CH N 0 304 Et H H CF₃ CF₃ H NMe CH N 1 305 Et H H CF₃ CF₃ HNMe CH N 2 306 Et H H H 2-chloro- H NMe CH N 0 phenyl 307 Et H H H3-chloro- H NMe CH N 0 phenyl 308 Et H H H 4-chloro- H NMe CH N 0 phenyl309 Et H H H 6-chloro-3- H NMe CH N 0 pyridyl 310 Et H H H 5-fluoro-3- HNMe CH N 0 pyridyl 311 Et H H H 3-pyridyl H NMe CH H 0 312 Et H H H4-pyridyl H NMe CH N 0 313 Et H H H 4-chloro-1- H NMe CH N 0 pyrazolyl314 Et H H H 2-chloro- H NMe CH N 1 phenyl 315 Et H H H 2-chloro- H NMeCH N 2 phenyl 316 Et H H H 3-chloro- H NMe CH N 1 phenyl 317 Et H H H3-chloro- H NMe CH N 2 phenyl 318 Et H H H 4-chloro- H NMe CH N 2 phenyl319 Et H H H 4-pyridyl H NMe CH N 1 320 Et H H H 4-pyridyl H NMe CH N 2321 Et H H H 6-chloro-3- H NMe CH N 2 pyridyl 322 Et H H H 5-fluoro-3- HNMe CH N 1 pyridyl 323 Et H H H 5-fluoro-3- H NMe CH N 2 pyridyl 324 EtH H H 4-chloro-1- H NMe CH N 2 pyrazolyl 325 Et H H H 3-chloro-1- H NMeCH N 0 triazolyl

TABLE 49 The present compound R¹ R² R³ R⁴ R⁵ R⁶ A¹ A² A³ n 326 Et H H H4-CF₃- H NMe CH N 0 imidazole 327 Et H H H 2-nitro-phenyl H NMe CH N 0328 Et H H H 3-nitro-phenyl H NMe CH N 0 329 Et H H H 2-cyano-phenyl HNMe CH N 0 330 Et H H H 3-cyano-phenyl H NMe CH N 0 331 Et H H H4-cyano-phenyl H NMe CH N 0 332 Et H H H 3-CF₃- H NMe CH N 0 triazolyl333 Et H H H 3-CF₃-5-Me- H NMe CH N 0 triazolyl 334 Et H H H 3-chloro-1-H NMe CH N 2 triazolyl 335 Et H H H 4-CF₃- H NMe CH N 1 imidazolyl 336Et H Br H CF₃ H NMe CH N 0 337 Et H Br H CF₃ H NMe CH N 1 338 Et H CN HCF₃ H NMe CH N 0 339 Et H CN H CF₃ H NMe CH N 1 340 Et H CN H CF₃ H NMeCH N 2 341 Et H CF₂CF₃ H CF₃ H NMe CH N 1 342 Et H CHO H CF₃ H NMe CH N0 343 Et H Ph H CF₃ H NMe CH N 0 344 Et H H H SMe H NMe CH N 0 345 Et HH H SO₂Me H NMe CH N 2 346 Et H H H SEt H NMe CH N 0 347 Et H H H SO₂EtH NMe CH N 2 348 Et H H H SiPr H NMe CH N 0 349 Et H H H SO₂iPr H NMe CHN 2 350 Et H H H SCH₂CF₃ H NMe CH N 0

TABLE 50 The present compound R¹ R² R³ R⁴ R⁵ R⁶ A¹ A² A³ n 351 Et H H HSO₂CH₂CF₃ H NMe CH N 2 352 Et H H H SCH₂CH═CH₂ H NMe CH N 0 353 Et H H HSCF₂CF₃ H NMe CH N 0 354 Et H H H SCF₂CF₂CF₃ H NMe CH N 0 355 Et H H HSCF(CF₃)₂ H NMe CH N 0 356 Et H H H CH(OH)CF₃ H NMe CH N 0 357 Et H H HCH(Cl)CF₃ H NMe CH N 0 358 Et H H H OH H NMe CH N 0 359 Et H H H OH HNMe CH N 2 360 Et H H H OCF₂Br H NMe CH N 2 361 Et H H H OCF₃ H NMe CH N2 362 Et H H H SCF₂CF₃ H NMe CH N 1 363 Et H H H SCF₂CF₂CF₃ H NMe CH N 1364 Et H H H SCF₂CF₂CF₃ H NMe CH N 2 365 Et H H H StBu H NMe CH N 0 366Et H H H SO₂tBu H NMe CH N 2 367 Et H CF₃ H Br H NMe CH N 0 368 Et H CF₃H Br H NMe CH N 1 369 Et H CF₃ H Br H NMe CH N 2 370 Et H H H SCH═C═CH₂H NMe CH N 0 371 Et H H H SO₂CH═C═CH₂ H NMe CH N 2 372 Et H H HSO₂CH₂CH═CH₂ H NMe CH N 2 373 Et H I H CF₂CF₃ H NMe CH N 2 374 Et H NO₂H CF₃ H NMe CH N 0 375 Et H NO₂ H CF₃ H NMe CH N 1

TABLE 51 The present compound R¹ R² R³ R⁴ R⁵ R⁶ A¹ A² A³ n 376 Et H NO₂H CF₃ H NMe CH N 2 377 Et H I H SCF₃ H NMe CH N 2 378 Et H I H SO₂CF₃ HNMe CH N 2 379 Et H Br H CF₂CF₃ H NMe CH N 2 380 Et H Cl H CF₃ H S CH N0 381 Et H Cl H CF₃ H S CH N 2 382 Et H H H C(OH)(CF₃)₂ H NMe CH N 0 383Et H H H C(Cl)(CF₃)₂ H NMe CH N 0 384 Et H H H C(Cl)(CF₃)₂ H NMe CH N 1385 Et H H H C(Cl)(CF₃)₂ H NMe CH N 2 386 Et H Cl H CF₂CF₃ H NMe CH N 2387 Et H H H H CF(CF₃)₂ NMe CH CH 0 388 Et H H H CF(CF₃)₂ H NMe CH CH 0389 Et H CF₃ H I H NMe CH N 2 390 Et H H H CF₂CF₃ H NMe CH CH 1 391 Et HH H SF₅ H NMe CH CH 1 392 Et H CF₃ H SF₅ H NMe CH CH 0 393 Et H CF₃ HSF₅ H NMe CH CH 1 394 Et H Me H CF₂CF₃ H NMe CH N 0 395 Et H Me H CF₂CF₃H NMe CH N 1 396 Et H Me H CF₂CF₃ H NMe CH N 2 397 Et H H H I H S CH N 0398 Et H CF₃ H I H S CH N 0 399 Et H H H CF₂CF₃ H S CH N 0 400 Et H CF₃H CF₂CF₃ H S CH N 0

TABLE 52 The present compound R¹ R² R³ R⁴ R⁵ R⁶ A¹ A² A³ n 401 Et H H HCF₂CF₃ H S CH N 2 402 Et H CF₃ H CF₂CF₃ H S CH N 2 403 Et H H H H CF₃ SN CH 0 404 Et H H H H CF₃ S N CH 2 405 Et H CH═CH₂ H CF₃ H NMe CH N 2406 Et H Et H CF₃ H NMe CH N 2 407 Et H H H SO₂NMe₂ H NMe CH N 1 408 EtH H H SO₂NMe₂ H NMe CH N 2 409 Et H H H CF₃ H NMe CH CNH₂ 0 410 Et H BrH SCF₃ H NMe CH N 2 411 Et H H H CF₃ H NMe CH CNMe₂ 0 412 Et H CF₃ H CF₃H NMe CH CNH₂ 0 413 Et H CF₃ H CF₃ H NMe CH CNMe₂ 0 414 Et H SF₅ H CF₃ HNMe CH N 0 415 Et H SF₅ H CF₃ H NMe CH N 1 416 Et H SF₅ H CF₃ H NMe CH N2 417 Et H H H CF(CF₃)₂ H NH CH CH 0 418 Et H H H Br H NMe CCF₂H N 0 419Et H H H Br H NMe CCF₂H N 1 420 Et H H H Br H NMe CCF₂H N 2 421 Et H H HBr H NMe CiPr N 0 422 Et H H H CF₃ H NH CH N 1 423 Et H H H CF₃ H NH CHCH 0 424 Et H CF₃ H CF₃ H NEt CH N 2 425 Et H CF₃ H CF₃ H NCH₂CH═CH₂ CHN 2

TABLE 53 The present compound R¹ R² R³ R⁴ R⁵ R⁶ A¹ A² A³ n 426 Et H CF₃H CF₃ H NCH₂CN CH N 2 427 Et H CF₃ H H CF₃ NCH₂CN N CH 2 428 Et H CF₃ HCF₃ H NCH₂OEt CH N 2 429 Et H CF₃ H H CF₃ NCH₂OEt N CH 2 430 Et H CF₃ HCF₃ H NCH₂SMe CH N 2 431 Et H CF₃ H CF₃ H NPr CH N 2 432 Et H CF₃ H CF₃H N(CH₂)₃CH₃ CH N 2 433 Et H CF₃ H CF₃ H NCH₂CO₂Me CH N 2 434 Et H CF₃ HH CF₃ NCH₂CO₂Me N CH 2 435 Et H CF₃ H CF₃ H NCH₂CH═CCl₂ CH N 2 436 Et HCF₃ H CF₃ H NCO₂tBu CH N 2 437 Et H CF₃ H CF₃ H NCO₂Me CH N 2 438 Et HCF₃ H CF₃ H NCOMe CH N 2 439 Et H OCF₃ H CF₃ H NMe CH N 0 440 Et H OCF₃H CF₃ H NMe CH N 1 441 Et H CF₂CF₂CF₂CF₃ H CF₃ H NMe CH N 2 442 Et H NH₂H CF₃ H NMe CH N 2 443 Et H NHCOCF₃ H CF₃ H NMe CH N 2 444 Et H iPr HCF₃ H NMe CH N 2 445 Et H CHO H CF₃ H NMe CH N 2 446 CH₂CH₂CH₂CH₃ H H HCF₃ H NMe CH N 0 447 CH₂CO₂Me H H H CF₃ H NMe CH N 0 448 CH₂CH═CCl₂ H HH CF₃ H NMe CH N 0 449 CH₂C≡CCH₃ H H H CF₃ H NMe CH N 0 450 CH₂CN H H HCF₃ H NMe CH N 0

TABLE 54 The present compound R¹ R² R³ R⁴ R⁵ R⁶ A¹ A² A³ n 451 CH₂tBu HH H CF₃ H NMe CH N 0 452 CH₂CH₂CN H H H CF₃ H NMe CH N 0 453 CH₂CycBu HH H CF₃ H NMe CH N 0 454 CF₂Br H H H CF₃ H NMe CH N 0 455 Et H CF₂H HCF₃ H NMe CH N 2 456 Et H CH₂OH H CF₃ H NMe CH N 2 457 (CH₂)₃CH₃ H H HCF₃ H NMe CH N 2 458 CH₂CO₂Me H H H CF₃ H NMe CH N 2 459 CH₂CH═CCl₂ H HH CF₃ H NMe CH N 2 460 CH₂C≡CCH₃ H H H CF₃ H NMe CH N 2 461 CH₂CN H H HCF₃ H NMe CH N 2 462 CH₂tBu H H H CF₃ H NMe CH N 2 463 CH₂CH₂CN H H HCF₃ H NMe CH N 2 464 CH₂CycBu H H H CF₃ H NMe CH N 2 465 CF₂Br H H H CF₃H NMe CH N 2 466 Et H CH₂F H CF₃ H NMe CH N 2 467 CH═CH₂ H H H CF₃ H NMeCH N 0 468 CH═CH₂ H H H CF₃ H NMe CH N 1 469 CH═CH₂ H H H CF₃ H NMe CH N2 470 Et H H H H CF₃ S CH N 0 471 Et H H H H CF₃ S CH N 2 472 Et H OCF₃H CF₂CF₃ H NMe CH N 0 473 Et H OCF₃ H CF₂CF₃ H NMe CH N 1 474 Et H OCF₃H CF₂CF₃ H NMe CH N 2 475 Et H CF₃ H CF₃ H NMe CH CMe 0

TABLE 55 The present compound R¹ R² R³ R⁴ R⁵ R⁶ A¹ A² A³ n 476 Et H CF₃H CF₃ H NMe CH CMe 1 477 Et H CF₃ H CF₃ H NMe CH CF 0 478 Et H CF₃ H CF₃H NMe CH CF 1 479 CH₂CycPr H H H CF₃ H NMe CH N 0 480 CH₂CycPr H H H CF₃H NMe CH N 1 481 Et H CF₃ H CF₃ H NMe CH CBr 0 482 Et H CF₃ H CF₃ H NMeCH CSCH₂CH₃ 0 483 CH₂C≡CH H H H CF₃ H NMe CH N 0 484 CH₂C≡CH H H H CF₃ HNMe CH N 2 485 Et H C≡CH H CF₃ H NMe CH N 2 486 Et H 4- H CF₃ H NMe CH N2 trifluoromethyl- 2- pyridyl 487 Et H OCF₃ H SCF₃ H NMe CH N 0 488 Et HOCF₃ H SCF₃ H NMe CH N 1 489 Et H OCF₃ H SCF₃ H NMe CH N 2 490 Et H CF₃H CF₃ H NMe CH CBr 1 491 Et H CF₃ H CF₃ H NMe CH CBr 2 492 Et H H H 2- HNMe CH N 0 pyridyl 493 Et H H H 2- H NMe CH N 2 pyridyl 494 Et H H H2-furyl H NMe CH N 0 495 Et H H H 2-furyl H NMe CH N 2 496 Et H H H 2- HNMe CH N 0 thienyl 497 Et H H H 2- H NMe CH N 2 thienyl 498 Et H H HCH═CH₂ H NMe CH N 0 499 Et H H H CH═CH₂ H NMe CH N 2 500 Et H H H COMe HNMe CH N 0

TABLE 56 The present compound R¹ R² R³ R⁴ R⁵ R⁶ A¹ A² A³ n 501 Et H H HCOMe H NMe CH N 2 502 Et H H H CH₂CH═CH₂ H NMe CH N 0 503 Et H H H CF₃ HN-(6- CH N 2 Chloro- pyridin-3- ylmethyl) 504 Et H CF₃ H CF₃ H N-(6- CHN 2 Chloro- pyridin-3- ylmethyl) 505 Et H H H CF₃ H N-(2- CH N 2 Chloro-thiazol-5- ylmethyl) 506 Et H CF₃ H CF₃ H N-(2- CH N 2 Chloro-thiazol-5- ylmethyl) 507 Et H H H CF₃ CN NMe CH N 2 508 Et H CF₃ H CF₃CN NMe CH N 2 509 Et H H H CF₃ H N-(2- CH N 0 Chloro- thiazol-5-ylmethyl) 510 Et H CF₃ H CF₃ H N-(2- CH N 0 Chloro- thiazol-5- ylmethyl) 511* Et H H H CF₃ H NMe CH N 2  512* Et H CF₃ H CF₃ H NMe CH N 2 513 EtH H H CF₃ H NMe CH COMe 0 514 Et H H H CF₃ H NMe CH CSMe 0 515 Et H H HCF₃ H NMe CH CSO₂Me 2 516 Et H H H CF₃ H NMe CH CSPh 0 517 Et H H H CF₃H NMe CH CSO₂Ph 2 518 Et H H H CF₃ H NMe CH CSO₂CH₂CF₃ 2 519 Et H H HCF₃ H NMe CH CCN 0 520 Et H CF₃ H CF₃ H NMe CNMe₂ N 2 521 Et H CF₃ H CF₃CO₂H NMe CH N 2 522 Et H CF₃ H CF₃ CONH₂ NMe CH N 2  523* Et H CF₃ HCF₂CF₃ H NMe CH N 2  524* Et H CF₃ H CF₂CF₃ H NMe CH N 2 525 Et H CF₃ HCO₂H H NMe CH N 0

TABLE 57 The present compound R¹ R² R³ R⁴ R⁵ R⁶ A¹ A² A³ n 526 Et H H HCF₃ H NMe CH CCN 1 527 Et H H H CF₃ H NH CH CCF₃ 0 528 Et H C(OMe)₃ HCF₂CF₃ H NMe CH N 2 529 Et H H H H CF₃ NMe CCF₃ CH 0 530 Et H H H H CF₃NMe CCF₃ CH 2 531 Et H H H CF₃ H NMe CH CCF₃ 2 532 Me H CF₃ H CF₂CF₃ HNMe CH N 0 533 Me H CF₃ H CF₂CF₃ H NMe CH N 2 534 Pr H CF₃ H CF₂CF₃ HNMe CH N 0 535 Pr H CF₃ H CF₂CF₃ H NMe CH N 2 536 iPr H CF₃ H CF₂CF₃ HNMe CH N 0 537 iPr H CF₃ H CF₂CF₃ H NMe CH N 2 538 Bu H CF₃ H CF₂CF₃ HNMe CH N 0 539 Bu H CF₃ H CF₂CF₃ H NMe CH N 2 540 CH(CH₃)CH₂CH₃ H CF₃ HCF₂CF₃ H NMe CH N 0 541 CH(CH₃)CH₂CH₃ H CF₃ H CF₂CF₃ H NMe CH N 2 542CH₂CH(CH₃)₂ H CF₃ H CF₂CF₃ H NMe CH N 0 543 CH₂CH(CH₃)₂ H CF₃ H CF₂CF₃ HNMe CH N 2 544 tBu H CF₃ H CF₂CF₃ H NMe CH N 0 545 tBu H CF₃ H CF₂CF₃ HNMe CH N 2 546 CycPen H CF₃ H CF₂CF₃ H NMe CH N 0 547 CycPen H CF₃ HCF₂CF₃ H NMe CH N 2 548 CycHex H CF₃ H CF₂CF₃ H NMe CH N 0 549 CycHex HCF₃ H CF₂CF₃ H NMe CH N 2 550 CH₂CF₃ H CF₃ H CF₂CF₃ H NMe CH N 0

TABLE 58 The present compound R¹ R² R³ R⁴ R⁵ R⁶ A¹ A² A³ n 551 CH₂CF₃ HCF₃ H CF₂CF₃ H NMe CH N 2 552 Et H CF₃ H CN H NMe CH N 0 553 Et H H HCF₃ H NMe CH CCF₃ 0 554 Et H CF₃ H CF₂CF₃ H N-(4- CH N 0 methoxy-benzyl) 555 Et H CF₃ H H CF₂CF₃ N-(4- N CH 0 methoxy- benzyl)

In the above [Table 36] to [Table 58], the symbol “*” in the presentcompound represents N-oxide. Specifically, the following compounds arementioned.

The Present Compound 22

The Present Compound 36

The Present Compound 37

The Present Compound 47

The Present Compound 48

The Present Compound 51

The Present Compound 70

The Present Compound 511

The Present Compound 512

The Present Compound 523

The Present Compound 524

In the above [Table 36] to [Table 58], “Me” represents a methyl group,“Et” represents an ethyl group, “Pr” represents a propyl group, “iPr”represents an isopropyl group, “Bu” represents a butyl group, “tBu”represents a tert-butyl group, “CycPr” represents a cyclopropyl group,“CycBu” represents a cyclobutyl group, “CycPen” represents a cyclopentylgroup, “CycHex” represents a cyclohexyl group, “Ph” represents a phenylgroup, “2-CF₃-Ph” represents a 2-trifluoromethylphenyl group, “3-CF₃-Ph”represents a 3-trifluoromethylphenyl group, “4-CF₃-Ph” represents a4-trifluoromethylphenyl group, “3-CF₃-triazolyl” represents a3-trifluoromethyl-(1H-1,2,4-triazol)-1-yl group, “3-CF₃-5-Me-triazolyl”represents a 3-trifluoromethyl-5-methyl-(1H-1,2,4-triazol)-1-yl group,and “4-CF₃-imidazolyl” represents a 4-trifluoromethylimidazole-1-ylgroup.

Hereinafter, ¹H-NMR data of the present compounds listed in [Table 36]to [Table 58] are shown.

The Present Compound 47

¹H-NMR (CDCl₃) δ: 8.53 (1H, dd), 8.07 (1H, s), 7.98 (1H, dd), 7.65 (1H,dd), 7.62-7.56 (2H, m), 3.90-3.77 (1H, m), 3.75 (3H, s), 3.52-3.42 (1H,m), 1.33 (3H, t).

The Present Compound 49

¹H-NMR (CDCl₃) δ: 8.61-7.00 (6H, m), 3.90 (3H, s), 2.94 (2H, q), 1.33(3H, t).

The Present Compound 50

¹H-NMR (CDCl₃) δ: 8.93 (1H, dd), 8.49 (1H, dd), 7.68-7.62 (2H, m), 7.43(1H, d), 7.25 (1H, d), 3.84 (2H, q), 3.73 (3H, s), 1.31 (3H, q).

The Present Compound 52

¹H-NMR (CDCl₃) δ: 8.48-8.44 (2H, m), 8.05 (1H, d), 7.74 (1H, dd), 7.65(1H, dd), 7.35 (1H, dd), 3.05 (2H, q), 1.49 (3H, t).

The Present Compound 53

¹H-NMR (CDCl₃) δ: 8.92 (1H, dd), 8.65 (1H, dd), 8.37 (1H, s), 8.11 (1H,d), 7.72 (1H, dd), 7.66 (1H, dd), 4.19 (2H, q), 1.45 (3H, t).

The Present Compound 54

¹H-NMR (CDCl₃) δ: 8.66 (1H, s), 8.50 (1H, s), 8.08 (1H, d), 7.90 (1H,s), 7.69 (1H, dd), 3.08 (2H, q), 1.52 (3H, t).

The Present Compound 55

¹H-NMR (CDCl₃) δ: 9.15 (1H, d), 8.88 (1H, d), 8.40 (1H, s), 8.14 (1H,d), 7.76 (1H, dd), 4.24 (2H, q), 1.49 (3H, t).

The Present Compound 56

¹H-NMR (CDCl₃) δ: 8.95 (1H, dd), 8.49 (1H, dd), 8.00 (1H, s), 7.66 (1H,dd), 6.96 (1H, s), 3.97 (3H, s), 3.84 (2H, q), 3.73 (3H, s), 1.34 (3H,t).

The Present Compound 57

¹H-NMR (DMSO-D₆) δ: 8.67 (1H, d), 8.56 (1H, dd), 8.23 (1H, d), 8.05 (1H,d), 7.91 (2H, s), 7.59 (1H, dd), 3.86 (3H, s), 3.00 (2H, q), 1.21 (3H,t).

The Present Compound 58

¹H-NMR (CDCl₃) 5; 9.20 (1H, d), 9.01 (1H, dd), 8.74 (1H, d), 8.54 (1H,dd), 7.76 (1H, dd), 3.89 (3H, s), 3.86-3.76 (2H, m), 1.37 (3H, t).

The Present Compound 59

¹H-NMR (CDCl₃) δ: 9.18 (1H, d), 8.82 (1H, d), 8.74 (1H, s), 7.92 (1H,s), 4.10 (3H, s), 4.00 (3H, s), 3.02 (2H, q), 1.40 (3H, t).

The Present Compound 60

¹H-NMR (CDCl₃) δ: 9.26 (1H, s), 8.82-8.78 (2H, m), 8.61 (1H, s),3.99-3.91 (5H, m), 1.42 (3H, t).

The Present Compound 61

¹H-NMR (CDCl₃) δ: 8.50 (1H, dd), 8.22 (1H, d), 7.77 (1H, dd), 7.63 (1H,dd), 7.46 (1H, d), 7.39-7.34 (1H, m), 3.92 (3H, s), 2.95 (2H, q), 1.34(3H, t).

The Present Compound 62

¹H-NMR (CDCl₃) δ: 8.79 (1H, d), 8.63 (1H, d), 8.13 (1H, s), 7.66-7.60(2H, m), 7.49 (1H, d), 4.23 (3H, s), 3.74-3.64 (1H, m), 3.13-3.03 (1H,m), 1.47 (3H, t).

The Present Compound 63

¹H-NMR (CDCl₃) δ: 8.95 (1H, dd), 8.50 (1H, dd), 8.12 (1H, d), 7.69-7.61(2H, m), 7.48 (1H, d), 3.86-3.80 (2H, m), 3.75 (3H, s), 1.34 (3H, t).

The Present Compound 64

¹H-NMR (CDCl₃) δ: 8.91 (1H, dd), 8.46-8.40 (2H, m), 7.91 (1H, d),7.69-7.61 (2H, m), 3.75-3.68 (5H, m), 1.25 (3H, t).

The Present Compound 69

¹H-NMR (CDCl₃) δ: 9.25 (1H, d), 9.20 (1H, d), 8.78 (1H, d), 8.73 (1H,d), 4.02-3.95 (5H, m), 3.94 (3H, s), 1.41 (3H, t).

The Present Compound 70

¹H-NMR (CDCl₃) δ: 9.26 (1H, d), 8.86 (1H, d), 8.76 (1H, d), 8.36 (1H,d), 4.34 (3H, s), 4.01 (3H, s), 3.81 (2H, q), 1.40 (3H, t).

The Present Compound 76

¹H-NMR (CDCl₃) δ: 8.75 (1H, s), 8.48 (2H, dd), 7.77 (1H, dd), 7.38 (1H,dd), 3.07 (2H, q), 1.50 (3H, t). (No NH proton was detected)

The Present Compound 77

¹H-NMR (CDCl₃) δ: 12.11 (1H, s), 8.98 (1H, dd), 8.80 (1H, s), 8.70 (1H,dd), 8.45 (1H, s), 7.70 (1H, dd), 4.30 (2H, q), 1.43 (3H, t).

The Present Compound 78

¹H-NMR (CDCl₃) δ: 8.75-8.70 (2H, m), 8.34 (1H, s), 7.96 (1H, d),3.14-3.07 (2H, m), 1.48 (3H, t). (No NH proton was detected)

The Present Compound 79

¹H-NMR (CDCl₃) δ: 11.63 (1H, brs), 9.19 (1H, d), 8.93 (1H, d), 8.83 (1H,d), 8.48 (1H, d), 4.35 (2H, q), 1.47 (3H, t).

The Present Compound 80

¹H-NMR (CDCl₃) δ: 8.75 (1H, dd), 8.62 (1H, dd), 8.46 (1H, d), 7.81 (1H,dd), 7.45 (1H, dd), 3.07 (2H, q), 1.46 (3H, t).

The Present Compound 81

¹H-NMR (CDCl₃) δ: 9.06 (1H, dd), 8.79 (1H, d), 8.58 (1H, dd), 8.43 (1H,d), 7.78 (1H, dd), 3.88 (2H, q), 1.44 (3H, t).

The Present Compound 82

¹H-NMR (CDCl₃) δ: 8.82 (1H, s), 8.79 (1H, s), 8.50 (1H, s), 7.96 (1H,s), 3.11 (2H, q), 1.50 (3H, t).

The Present Compound 83

¹H-NMR (CDCl₃) δ: 9.29 (1H, s), 8.84 (1H, s), 8.81 (1H, d), 8.47 (1H,d), 3.96 (2H, q), 1.48 (3H, t).

The Present Compound 84

¹H-NMR (CDCl₃) δ: 8.59 (1H, dd), 8.24-8.21 (1H, m), 7.81-7.76 (2H, m),7.69 (1H, dd), 7.42 (1H, dd), 3.06 (2H, q), 1.47 (3H, t).

The Present Compound 85

¹H-NMR (CDCl₃) δ: 9.03 (1H, dd), 8.60 (1H, dd), 8.16-8.13 (1H, m),7.82-7.71 (3H, m), 4.01 (2H, q), 1.43 (3H, t):

The Present Compound 86

¹H-NMR (CDCl₃) δ: 8.79 (1H, dd), 8.26 (1H, dd), 7.94 (1H, d), 7.81 (1H,dd), 7.76-7.72 (1H, m), 3.11 (2H, q), 1.50 (3H, t).

The Present Compound 87

¹H-NMR (CDCl₃) δ: 9.25 (1H, d), 8.83 (1H, d), 8.18 (1H, s), 7.85-7.76(2H, m), 4.08 (2H, q), 1.47 (3H, t).

The Present Compound 89

¹H-NMR (CDCl₃) δ: 9.25 (1H, d), 8.78 (1H, d), 8.43 (1H, s), 3.97-3.87(5H, m), 1.41 (3H, t).

The Present Compound 99

¹H-NMR (CDCl₃) δ: 9.20 (1H, d), 8.76 (1H, d), 8.26 (1H, s), 4.02 (2H,q), 3.84 (3H, s), 3.04 (6H, s), 1.41 (3H, t).

The Present Compound 130

¹HNMR (CDCl₃) δ: 9.01 (1H, dd), 8.68 (1H, d), 8.55 (1H, dd), 8.37 (1H,d), 7.74 (1H, dd), 3.87 (3H, s), 3.83 (2H, q), 1.37 (3H, t).

The Present Compound 138

¹H-NMR (CDCl₃) δ: 9.02 (1H, dd), 8.54 (1H, dd), 8.28 (1H, s), 7.95 (1H,s), 7.77 (1H, dd), 4.06 (3H, s), 3.74 (2H, q), 1.35 (3H, t).

The Present Compound 144

¹H-NMR (CDCl₃) δ: 9.00-8.95 (1H, m), 8.54-8.47 (1H, m), 7.71-7.64 (2H,m), 6.94 (1H, s), 4.00 (3H, s), 3.96 (3H, s), 3.81-3.70 (2H, m),1.37-1.29 (3H, m).

The Present Compound 190

¹H-NMR (CDCl₃) δ: 8.99 (1H, dd), 8.65 (1H, d), 8.53 (1H, dd), 8.38 (1H,d), 7.71 (1H, dd), 3.83-3.80 (5H, m), 1.35 (3H, t).

The Present Compound 255

¹H-NMR (CDCl₃) δ: 8.78 (1H, d), 8.73-8.71 (1H, m), 8.65 (1H, d),8.31-8.30 (1H, m), 4.35 (3H, s), 3.73-3.63 (1H, m), 3.16-3.06 (1H, m),1.48 (3H, t)

The Present Compound 386

¹H-NMR (CDCl₃) δ: 8.95 (1H, d), 8.72-8.71 (1H, m), 8.53 (1H, d),8.30-8.28 (1H, m), 3.94-3.87 (5H, m), 1.40 (3H, t)

The Present Compound 505

¹H-NMR (CDCl₃) δ: 9.05 (1H, dd), 8.79 (1H, t), 8.60 (1H, dd), 8.33 (1H,d), 7.78 (1H, dd), 7.58 (1H, s), 5.66 (2H, s), 3.98 (2H, q), 1.40 (3H,t).

The Present Compound 506

1H-NMR (CDCl₃) δ: 9.30 (1H, d), 8.84 (1H, d), 8.82 (1H, d), 8.36 (1H,d), 7.64 (1H, s), 5.70 (2H, s), 4.09 (2H, q), 1.45 (3H, t).

The Present Compound 508

¹H-NMR (CDCl₃) δ: 9.28 (1H, d), 8.79 (1H, d), 8.48 (1H, s), 3.96 (3H,s), 3.89 (2H, q), 1.42 (3H, t).

The Present Compound 509

¹H-NMR (CDCl₃) δ: 8.75 (1H, d), 8.58 (1H, dd), 8.42 (1H, d), 7.82 (1H,dd), 7.66 (1H, s), 7.44 (1H, dd), 5.96 (2H, s), 2.98 (2H, q), 1.37 (3H,t).

The Present Compound 510

¹H-NMR (CDCl₃) δ: 8.80 (2H, dd), 8.46 (1H, d), 7.97 (1H, d), 7.71 (1H,s), 5.99 (2H, s), 3.04 (2H, q), 1.42 (3H, t).

The Present Compound 511

¹H-NMR (CDCl₃) δ: 8.53 (1H, dd), 8.48 (1H, d), 7.98 (1H, dd), 7.93 (1H,d), 7.71 (1H, dd), 4.27 (3H, s), 3.73-3.63 (1H, m), 3.47-3.37 (1H, m),1.35 (3H, t).

The Present Compound 512

¹H-NMR (CDCl₃) δ: 8.75 (1H, d), 8.49 (1H, d), 8.12 (1H, d), 7.94 (1H,d), 4.28 (3H, s), 3.75-3.65 (1H, m), 3.55-3.45 (1H, m), 1.38 (3H, t).

The Present Compound 513

¹H-NMR (CDCl₃) δ: 8.49 (1H, d), 7.76-7.74 (2H, m), 7.35 (1H, dd), 6.91(1H, s), 4.05 (3H, s), 3.99 (3H, s), 2.95-2.85 (2H, m), 1.34-1.24 (3H,m).

The Present Compound 514

¹H-NMR (CDCl₃) δ: 8.51 (1H, d), 7.97 (1H, s), 7.77 (1H, d), 7.42 (1H,s), 7.37 (1H, dd), 4.18 (3H, s), 2.91 (2H, q), 2.59 (3H, s), 1.30 (3H,t).

The Present Compound 515

¹H-NMR (CDCl₃) δ: 9.08-8.97 (1H, m), 8.58-8.46 (1H, m), 8.41-8.26 (2H,m), 7.84-7.70 (1H, m), 4.12 (3H, s), 3.72-3.59 (2H, m), 3.33 (3H, s),1.39-1.22 (3H, m).

The Present Compound 516

¹H-NMR (CDCl₃) δ: 8.49 (1H, dd), 8.18 (1H, d), 7.75 (1H, dd), 7.71 (1H,d), 7.50-7.48 (1H, m), 7.36 (1H, dd), 7.30-7.09 (4H, m), 4.02 (3H, s),2.90 (2H, q), 1.28 (3H, t).

The Present Compound 517

¹H-NMR (CDCl₃) δ: 8.97 (1H, dd), 8.49 (1H, dd), 8.31 (1H, d), 8.17 (1H,d), 7.89 (2H, d), 7.72 (1H, dd), 7.69-7.64 (1H, m), 7.61-7.55 (2H, m),3.87 (3H, s), 3.67 (2H, q), 1.32 (3H, t).

The Present Compound 518

¹H-NMR (CDCl₃) δ: 9.02-8.97 (1H, m), 8.54-8.49 (1H, m), 8.33 (1H, s),8.23 (1H, s), 7.80-7.71 (1H, m), 4.03-3.88 (3H, m), 3.75-3.63 (4H, m),1.36-1.30 (3H, m).

The Present Compound 519

¹H-NMR (CDCl₃) δ: 8.55 (1H, dd), 8.37-8.35 (1H, m), 7.93-7.92 (1H, m),7.81 (1H, dd), 7.43 (1H, dd), 4.19 (3H, s), 2.96 (2H, q), 1.33 (3H, t).

The Present Compound 520

¹H-NMR (CDCl₃) δ: 9.22 (1H, t), 8.77 (1H, d), 8.53 (1H, s), 3.95 (2H,q), 3.84 (3H, s), 3.33 (6H, s), 1.41 (3H, t).

The Present Compound 521

¹H-NMR (CDCl₃) δ: 9.28 (1H, d), 8.80 (1H, d), 8.62 (1H, s), 3.97 (3H,s), 3.89 (2H, q), 1.42 (3H, t). (No active proton was detected)

The Present Compound 522

¹H-NMR (CDCl₃) δ: 9.27 (1H, d), 8.79 (1H, d), 8.56 (1H, s), 7.24 (1H,brs), 5.76 (1H, brs), 4.00-3.86 (5H, m), 1.42 (3H, t).

The Present Compound 523

¹H-NMR (CDCl₃) b: 9.27 (1H, d), 8.77 (1H, d), 8.45 (1H, s), 7.92 (1H,s), 4.34 (3H, s), 3.81 (2H, q), 1.40 (3H, t).

The Present Compound 524

¹H-NMR (CDCl₃) δ: 8.80 (1H, s), 8.46 (1H, s), 8.13 (1H, s), 7.93 (1H,s), 4.27 (3H, s), 3.76-3.66 (1H, m), 3.55-3.45 (1H, m), 1.38 (3H, t).

The Present Compound 525

¹H-NMR (DMSO-D₆) δ: 9.06 (1H, d), 8.95 (1H, s), 8.63 (1H, d), 8.31 (1H,s), 3.95 (3H, s), 3.15 (2H, q), 1.23 (3H, t). (No active proton wasdetected)

The Present Compound 526

¹H-NMR (CDCl₃) δ: 8.87 (1H, dd), 8.67 (1H, dd), 8.29 (1H, d), 7.96 (1H,d), 7.72 (1H, dd), 4.57 (3H, s), 3.73-3.62 (1H, m), 3.17-3.07 (1H, m),1.48 (3H, t).

The Present Compound 527

¹H-NMR (CDCl₃) δ: 10.95 (1H, s), 8.46-8.42 (2H, m), 7.82 (1H, s), 7.76(1H, dd), 7.38 (1H, dd), 3.07 (2H, q), 1.50 (3H, t).

The Present Compound 528

¹H-NMR (CDCl₃) δ: 9.16 (1H, d), 8.74 (1H, d), 8.70 (1H, d), 8.31 (1H,d), 3.93 (3H, s), 3.88 (2H, q), 3.28 (9H, s), 1.38 (3H, t).

The Present Compound 529

¹H-NMR (CDCl₃) δ: 8.51-8.46 (1H, m), 7.94 (1H, s), 7.86 (1H, s),7.80-7.76 (1H, m), 7.40-7.35 (1H, m), 3.96 (3H, s), 2.96-2.90 (2H, m),1.31-1.25 (3H, m).

The Present Compound 530

¹H-NMR (CDCl₃) δ: 8.99 (1H, dd), 8.54 (1H, dd), 7.97 (1H, s), 7.87 (1H,s), 7.72 (1H, dd), 3.95-3.88 (5H, m), 1.37 (3H, t).

The Present Compound 531

¹H-NMR (CDCl₃) δ: 8.93 (1H, dd), 8.45 (1H, dd), 8.19 (1H, s), 7.87 (1H,s), 7.66 (1H, dd), 3.77-3.75 (3H, m), 3.63 (2H, q), 1.26 (3H, t).

The Present Compound 532

¹H-NMR (CDCl₃) δ: 8.75 (1H, s), 8.72 (1H, s), 8.41 (1H, s), 7.90 (1H,s), 4.15 (3H, s), 2.54 (3H, s)

The Present Compound 533

¹H-NMR (CDCl₃) δ: 9.25 (1H, s), 8.85 (1H, s), 8.75 (1H, s), 8.32 (1H,s), 3.96 (3H, s), 3.73 (3H, s)

The Present Compound 534

¹H-NMR (CDCl₃) δ: 8.74 (1H, s), 8.71 (1H, s), 8.41 (1H, s), 7.93 (1H,s), 4.10 (3H, s), 2.97 (2H, t), 1.82-1.71 (2H, m), 1.08 (3H, t)

The Present Compound 535

¹H-NMR (CDCl₃) δ: 9.24 (1H, s), 8.79 (1H, s), 8.74 (1H, s), 8.31 (1H,s), 3.95-3.88 (5H, m), 1.92-1.81 (2H, m), 1.13 (3H, t)

The Present Compound 536

¹H-NMR (CDCl₃) δ: 8.76 (1H, s), 8.71 (1H, s), 8.41 (1H, s), 8.01 (1H,s), 4.07 (3H, s), 3.64-3.53 (1H, m), 1.38 (6H, d)

The Present Compound 537

¹H-NMR (CDCl₃) δ: 9.24 (1H, s), 8.75 (2H, d), 8.31 (1H, s), 4.71-4.60(1H, m), 3.93 (3H, s), 1.39 (6H, d)

The Present Compound 538

¹H-NMR (CDCl₃) δ: 8.74 (1H, s), 8.71 (1H, s), 8.41 (1H, s), 7.94 (1H,s), 4.10 (3H, s), 2.98 (2H, t), 1.76-1.67 (2H, m), 1.55-1.44 (2H, m),0.95 (3H, t)

The Present Compound 539

¹H-NMR (CDCl₃) δ: 9.24 (1H, s), 8.79 (1H, s), 8.74 (1H, s), 8.29 (1H,s), 3.97-3.91 (5H, m), 1.85-1.77 (2H, m), 1.59-1.48 (2H, m), 0.99 (3H,t)

The Present Compound 540

¹H-NMR (CDCl₃) δ: 8.76 (1H, s), 8.71 (1H, s), 8.40 (1H, s), 8.00 (1H,s), 4.05 (3H, s), 3.40-3.30 (1H, m), 1.80-1.55 (2H, m), 1.35 (3H, d),1.02 (3H, t)

The Present Compound 541

¹H-NMR (CDCl₃) δ: 9.23 (1H, s), 8.75 (2H, s), 8.28 (1H, s), 4.54-4.44(1H, m), 3.92 (3H, s), 2.02-1.91 (1H, m), 1.71-1.57 (1H, m), 1.37 (3H,d), 1.07 (3H, t)

The Present Compound 542

¹H-NMR (CDCl₃) δ: 8.74-8.73 (1H, m), 8.72-8.71 (1H, m), 8.41 (1H, d),7.92 (1H, d), 4.09 (3H, s), 2.86 (2H, d), 2.03-1.91 (1H, m), 1.08 (6H,d)

The Present Compound 543

¹H-NMR (CDCl₃) δ: 9.24 (1H, s), 8.81 (1H, s), 8.75 (1H, s), 8.28 (1H,s), 3.93 (3H, s), 3.87 (2H, d), 2.42-2.30 (1H, m), 1.15 (6H, d)

The Present Compound 544

¹H-NMR (CDCl₃) δ: 8.98 (1H, dd), 8.71 (1H, d), 8.37 (1H, d), 8.35-8.32(1H, m), 3.88 (3H, s), 1.26 (9H, s)

The Present Compound 545

¹H-NMR (CDCl₃) δ: 9.26 (1H, s), 8.71 (1H, s), 8.66 (1H, s), 8.29 (1H,s), 3.71 (3H, s), 1.41 (9H, s)

The Present Compound 546

¹H-NMR (CDCl₃) δ: 8.73 (1H, s), 8.71 (1H, s), 8.41 (1H, s), 8.02 (1H,s), 4.10 (3H, s), 3.72-3.64 (1H, m), 2.27-2.16 (2H, m), 1.85-1.62 (6H,m)

The Present Compound 547

¹H-NMR (CDCl₃) δ: 9.23 (1H, s), 8.76 (1H, s), 8.74 (1H, s), 8.31 (1H,s), 4.88-4.79 (1H, m), 3.90 (3H, s), 2.14-1.83 (6H, m), 1.80-1.69 (2H,m)

The Present Compound 548

¹H-NMR (CDCl₃) δ: 8.76-8.74 (1H, m), 8.71-8.70 (1H, m), 8.41-8.39 (1H,m), 8.01-7.99 (1H, m), 4.05 (3H, s), 3.36-3.27 (1H, m), 2.07-1.22 (10H,m)

The Present Compound 549

¹H-NMR (CDCl₃) δ: 9.23 (1H, s), 8.74 (1H, s), 8.72 (1H, s), 8.28 (1H,s), 4.43-4.34 (1H, m), 3.92 (3H, s), 2.03-1.20 (10H, m)

The Present Compound 550

¹H-NMR (CDCl₃) δ: 8.90 (1H, s), 8.74 (1H, s), 8.40 (1H, s), 8.18 (1H,s), 4.13 (3H, s), 3.68 (2H, q)

The Present Compound 551

¹H-NMR (CDCl₃) δ: 9.30-9.28 (1H, m), 8.87-8.85 (1H, m), 8.78-8.76 (1H,m), 8.36-8.34 (1H, m), 5.16 (2H, q), 4.04 (3H, s)

The Present Compound 552

¹H-NMR (CDCl₃) δ: 8.66 (1H, d), 8.63 (1H, d), 8.36 (1H, d), 7.87 (1H,d), 4.00 (3H, s), 2.95 (2H, q), 1.30 (3H, t).

The Present Compound 553

¹H-NMR (CDCl₃) δ: 8.55 (1H, dd), 8.35 (1H, s), 7.93 (1H, s), 7.81 (1H,dd), 7.43 (1H, dd), 3.95-3.93 (3H, m), 2.95 (2H, q), 1.32 (3H, t).

The Present Compound 554

¹H-NMR (CDCl₃) δ: 8.72 (2H, d), 8.41 (1H, d), 7.83 (1H, d), 6.98 (2H,d), 6.68 (2H, d), 5.81 (2H, s), 3.71 (3H, s), 2.89 (2H, q), 1.27 (3H,t).

The Present Compound 555

¹H-NMR (CDCl₃) δ: 8.83 (1H, d), 8.71 (1H, s), 7.90 (1H, s), 7.84 (1H,d), 7.05 (2H, d), 6.78 (2H, d), 5.65 (2H, s), 3.75 (3H, s), 2.97 (2H,q), 1.32 (3H, t).

A compound represented by the formula (M3):

wherein R¹, R², R³, R⁴, R⁵, R⁶, A¹, A², A³ and n represent any one ofthe combinations as listed in the following [Table 59] to [Table 61].The intermediate compound (M3) represented by the formula (M3) can besynthesized in the same manner as in Production process 2 or Productionprocess 7.

TABLE 59 Intermediate compound R¹ R² R³ R⁴ R⁵ R⁶ A¹ A² A³ n M3-1 Et H HH CF₃ H NMe CH N 0 M3-2 Et H H H CF₃ H NMe CH N 1 M3-3 Et H H H CF₃ HNMe CH N 2 M3-4 Et H CF₃ H CF₃ H NMe CH N 0 M3-5 Et H CF₃ H CF₃ H NMe CHN 2 M3-6 Et H H H CF₂CF₃ H NMe CH N 0 M3-7 Et H H H CF₂CF₃ H NMe CH N 1M3-8 Et H H H CF₂CF₃ H NMe CH N 2 M3-9 Et H H H I H NMe CH N 0 M3-10 EtH CF₃ H CF₃ H S CH N 0 M3-11 Et H CF₃ H CF₃ H S CH N 2 M3-12 Et H H HCF₃ H S CH N 2 M3-13 Et H H H SCF₃ H NMe CH N 0 M3-14 Et H H H SCF₃ HNMe CH N 1 M3-15 Et H H H SCF₃ H NMe CH N 2 M3-16 Et H H H SO₂CF₃ H NMeCH N 2 M3-17 Et H CF₃ H CF₂CF₃ H NMe CH N 0 M3-18 Et H CF₃ H CF₂CF₃ HNMe CH N 1 M3-19 Et H CF₃ H CF₂CF₃ H NMe CH N 2 M3-20 Et H H H SOCF₃ HNMe CH N 2 M3-21 Et H H H I H NMe CH CH 0 M3-22 Et H H H SF5 H NMe CH CH0 M3-23 Et H H H SF5 H NMe CH CH 2 M3-24 Et H CF₃ H SO₂CF₃ H NMe CH N 2

TABLE 60 Intermediate compound R¹ R² R³ R⁴ R⁵ R⁶ A¹ A² A³ n M3-25 Et H HH CF₂CF₃ H NMe CH CH 0 M3-26 Et H H H CF₂CF₃ H NMe CH CH 2 M3-27 Et HCF₃ H SCF₃ H NMe CH N 0 M3-28 Et H CF₃ H SCF₃ H NMe CH N 1 M3-29 Et H HH CF₃ H NMe CH CH 0 M3-30 Et H H H CF₃ H NMe CH CH 1 M3-31 Et H H H CF₃H NMe CH CH 2 M3-32 Et H CF₃ H CF₃ H NMe CH CH 0 M3-33 Et H CF₃ H CF₃ HNMe CH CH 1 M3-34 Et H CF₃ H CF₃ H NMe CH CH 2 M3-35 Et H CF₃ H CF₂CF₃ HNMe CH CH 0 M3-36 Et H CF₃ H CF₂CF₃ H NMe CH CH 1 M3-37 Et H CF₃ HCF₂CF₃ H NMe CH CH 2 M3-38 Et H H H CF3 H S CH N 0 M3-39 Et H CF₃ H I HNMe CH N 0 M3-40 Et H CF₃ H SCF₃ H NMe CH N 2 M3-41 Et H CF₃ H I H NMeCH CH 0 M3-42 Et H H H CF₃ H NMe CH CBr 0 M3-43 Et H H H CF₃ H N(CH₂CF₃)CH N 0 M3-44 Et H CF₃ H CF₃ H N(CH₂CF₃) CH N 0 M3-45 Et H CF₂CF₃ H CF₃ HNMe CH N 0 M3-46 Et H CF₂CF₃ H CF₂CF₃ H NMe CH N 0 M3-47 Et H H H CF₃ HNH CH N 0 M3-48 Et H CF₃ H CF₃ H NH CH N 0 M3-49 Et H H H CF₃ H OH CH N0 M3-50 Et H CF₃ H CF₃ H OH CH N 0

TABLE 61 Inter- mediate com- pound R¹ R² R³ R⁴ R⁵ R⁶ A¹ A² A³ n M3-51 EtH H H CF₃ H OH CH CH 0 M3-52 Et H CF₃ H CF₃ H OH CH CH 0 M3-53 Et H H HCF₃ H N-(2-Chloro- CH N 0 thiazol-5- ylmethyl) M3-54 Et H CF₃ H CF₃ HN-(2-Chloro- CH N 0 thiazol-5- ylmethyl) M3-55 Et H H H CF₃ H NH CH CCF₃0 M3-56 Et H H H CF₃ H NMe CH CCN 0

A compound represented by the formula (M6):

wherein V², R², R³, R⁴, R⁵, R⁶, A¹, A² and A³ represent any one of thecombinations as listed in the following [Table 62] to [Table 63]. Theintermediate compound (M6) represented by the formula (M6) can besynthesized in the same manner as in Production process 6.

TABLE 62 Intermediate compound V R² R³ R⁴ R⁵ R⁶ A¹ A² A³ M6-1 Cl H H HCF₃ H NMe CH N M6-2 F H H H CF₃ H NMe CH N M6-3 Cl H CF₃ H CF₃ H NMe CHN M6-4 F H CF₃ H CF₃ H NMe CH N M6-5 Cl H H H CF₂CF₃ H NMe CH N M6-6 F HH H CF₂CF₃ H NMe CH N M6-7 Cl H H H I H NMe CH N M6-8 F H H H I H NMe CHN M6-9 Cl H CF₃ H CF₃ H S CH N M6-10 F H CF₃ H CF₃ H S CH N M6-11 Cl H HH CF₃ H S CH N M6-12 F H H H CF₃ H S CH N M6-13 Cl H H H SCF₃ H NMe CH NM6-14 F H H H SCF₃ H NMe CH N M6-15 Cl H H H SO₂CF₃ H NMe CH N M6-16 F HH H SO₂CF₃ H NMe CH N M6-17 Cl H CF₃ H CF₂CF₃ H NMe CH N M6-18 F H CF₃ HCF₂CF₃ H NMe CH N M6-19 Cl H H H SOCF₃ H NMe CH N M6-20 F H H H SOCF₃ HNMe CH N M6-21 Cl H H H I H NMe CH CH M6-22 F H H H I H NMe CH CH M6-23Cl H H H SF₅ H NMe CH CH M6-24 F H H H SF₅ H NMe CH CH

TABLE 63 Intermediate compound V R² R³ R⁴ R⁵ R⁶ A¹ A² A³ M6-25 Cl H CF₃H SO₂CF₃ H NMe CH N M6-26 F H CF₃ H SO₂CF₃ H NMe CH N M6-27 Cl H H HCF₂CF₃ H NMe CH CH M6-28 F H H H CF₂CF₃ H NMe CH CH M6-29 Cl H H H CF₃ HNMe CH CH M6-30 F H H H CF₃ H NMe CH CH M6-31 Cl H CF₃ H CF₃ H NMe CH CHM6-32 F H CF₃ H CF₃ H NMe CH CH M6-33 Cl H CF₃ H CF₂CF₃ H NMe CH CHM6-34 F H CF₃ H CF₂CF₃ H NMe CH CH M6-35 Cl H CF₃ H I H NMe CH N M6-36 FH CF₃ H I H NMe CH N M6-37 Cl H CF₃ H SH H NMe CH N M6-38 F H CF₃ H SH HNMe CH N M6-39 Cl H CF₃ H SCF₃ H NMe CH N M6-40 F H CF₃ H SCF₃ H NMe CHN M6-41 Cl H CF₃ H I H NMe CH CH M6-42 F H CF₃ H I H NMe CH CH M6-43 ClH H H CF₃ H NMe CH CBr M6-44 Cl H H H CF₃ OCH₃ NMe CH CH M6-45 Cl H H HSCF₃ H NMe CH CH M6-46 Cl H H H CF₃ H S CH CH

A compound represented by the formula (M20):

wherein V², R², R³, R⁴, R⁵, R⁶, A¹, A² and A³ represent any one of thecombinations as listed in the following [Table 64] to [Table 65]. Theintermediate compound (M20) represented by the formula (M20) can besynthesized in the same manner as in Production process 6.

TABLE 64 Intermediate compound V R² R³ R⁴ R⁵ R⁶ A¹ A² A³ M20-1 Cl H H HCF₃ H NMe CH N M20-2 F H H H CF₃ H NMe CH N M20-3 Cl H CF₃ H CF₃ H NMeCH N M20-4 F H CF₃ H CF₃ H NMe CH N M20-5 Cl H H H CF₂CF₃ H NMe CH NM20-6 F H H H CF₂CF₃ H NMe CH N M20-7 Cl H H H I H NMe CH N M20-8 F H HH I H NMe CH N M20-9 Cl H CF₃ H CF₃ H S CH N M20-10 F H CF₃ H CF₃ H S CHN M20-11 Cl H H H CF₃ H S CH N M20-12 F H H H CF₃ H S CH N M20-13 Cl H HH SCF₃ H NMe CH N M20-14 F H H H SCF₃ H NMe CH N M20-15 Cl H H H SO₂CF₃H NMe CH N M20-16 F H H H SO₂CF₃ H NMe CH N M20-17 Cl H CF₃ H CF₂CF₃ HNMe CH N M20-18 F H CF₃ H CF₂CF₃ H NMe CH N M20-19 Cl H H H SOCF₃ H NMeCH N M20-20 F H H H SOCF₃ H NMe CH N M20-21 Cl H H H I H NMe CH CHM20-22 F H H H I H NMe CH CH M20-23 Cl H H H SF5 H NMe CH CH M20-24 F HH H SF5 H NMe CH CH

TABLE 65 Intermediate compound V R² R³ R⁴ R⁵ R⁶ A¹ A² A³ M20-25 Cl H CF₃H SO₂CF₃ H NMe CH N M20-26 F H CF₃ H SO₂CF₃ H NMe CH N M20-27 Cl H H HCF₂CF₃ H NMe CH CH M20-28 F H H H CF₂CF₃ H NMe CH CH M20-29 Cl H H H CF₃H NMe CH CH M20-30 F H H H CF₃ H NMe CH CH M20-31 Cl H CF₃ H CF₃ H NMeCH CH M20-32 F H CF₃ H CF₃ H NMe CH CH M20-33 Cl H CF₃ H CF₂CF₃ H NMe CHCH M20-34 F H CF₃ H CF₂CF₃ H NMe CH CH M20-35 Cl H CF₃ H I H NMe CH NM20-36 F H CF₃ H I H NMe CH N M20-37 Cl H CF₃ H SH H NMe CH N M20-38 F HCF₃ H SH H NMe CH N M20-39 Cl H CF₃ H SCF₃ H NMe CH N M20-40 F H CF₃ HSCF₃ H NMe CH N M20-41 Cl H CF₃ H I H NMe CH CH M20-42 F H CF₃ H I H NMeCH CH M20-43 Cl H H H CF₃ H NMe CH CBr M20-44 Cl H H H SCF₃ H NMe CH CH

A compound represented by the formula (P9′):

wherein R¹, R², R³, R⁴, R⁶, A¹, A², A³ and n represent any one of thecombinations as listed in the following [Table 66]. The intermediatecompound (P9′) represented by the formula (P9′) can be synthesized inthe same manner as in Production process 20.

TABLE 66 Intermediate compound R¹ R² R³ R⁴ R⁶ A¹ A² A³ n P9′-1 Et H H HH NMe CH N 0 P9′-2 Et H H H H NMe CH N 1 P9′-3 Et H H H H NMe CH N 2P9′-4 Et H CF₃ H H NMe CH N 0 P9′-5 Et H CF₃ H H NMe CH N 1 P9′-6 Et HCF₃ H H NMe CH N 2

A compound represented by the formula (M2):

wherein R¹, R², R³, R⁴ and n represent any one of the combinations aslisted in the following [Table 67]. The intermediate compound (M2)represented by the formula (M2) can be synthesized in the same manner asin Production process 12 or Production process 14.

TABLE 67 Intermediate compound R¹ R² R³ R⁴ n M2-1 Et H H H 0 M2-2 Et H HH 1 M2-3 Et H H H 2 M2-4 Et H CF₃ H 0 M2-5 Et H CF₃ H 1 M2-6 Et H CF₃ H2 M2-7 Et H CF₂CF₃ H 2

A compound represented by the formula (M18):

wherein R¹, R², R³, R⁴ and n represent any one of the combinations aslisted in the following [Table 68]. The intermediate compound (M18)represented by the formula (M18) can be synthesized in the same manneras in Production process 13.

TABLE 68 Intermediate compound R¹ R² R³ R⁴ n M18-1 Et H H H 0 M18-2 Et HH H 1 M18-3 Et H H H 2 M18-4 Et H CF₃ H 0 M18-5 Et H CF₃ H 1 M18-6 Et HCF₃ H 2

A compound represented by the formula (M37):

wherein R¹, R², R³, R⁴ and n represent any one of the combinations aslisted in the following [Table 69]. The intermediate compound (M37)represented by the formula (M37) can be synthesized in the same manneras in Production process 14.

TABLE 69 Intermediate compound R¹ R² R³ R⁴ n M37-1 Et H H H 0 M37-2 Et HH H 1 M37-3 Et H H H 2 M37-4 Et H CF₃ H 0 M37-5 Et H CF₃ H 1 M37-6 Et HCF₃ H 2

NMR data of the intermediate compounds M3-33, M3-47, M3-48, M3-49,M3-50, M3-51, M3-52, M3-53, M3-54, M3-55, M3-56, M6-1, M6-17, M6-44,M6-45, M6-46, M2-1, M2-4, M18-1, M20-44, M37-1 and M37-4 are shown inthe following [Table 70] to [Table 71].

TABLE 70 Intermediate compound Material value M3-33 ¹H-NMR (CDCl₃) δ:9.61 (1H, s), 8.96 (2H, d), 7.72 (1H, s), 7.49 (1H, d), 6.83 (1H, d),4.21 (1H, s), 3.38 (1H, brs), 2.94-2.94 (4H, brm), 1.36-1.23 (3H, m).M3-47 ¹H-NMR (CDCl₃) δ: 9.87 (1H, brs), 8.33 (1H, dd), 8.25 (1H, d),8.14 (1H, d), 7.75 (1H, dd), 7.44 (1H, dd), 5.01 (2H, brs), 2.96 (2H,q), 1.44 (3H, t). M3-48 ¹H-NMR (CDCl₃) δ: 9.73 (1H, s), 8.56 (1H, dd),8.28 (1H, dd), 8.12 (1H, d), 7.91 (1H, d), 4.99 (2H, s), 3.00 (2H, q),1.46 (3H, t). M3-49 ¹H-NMR (CDCl₃) δ: 12.34 (1H, s), 10.99 (1H, s), 8.75(1H, d), 8.39 (1H, dd), 7.76 (1H, dd), 7.45 (1H, dd), 7.38 (1H, d), 2.98(2H, q), 1.44 (3H, t). M3-50 ¹H-NMR (CDCl₃) δ: 11.36 (1H, s), 10.93 (1H,s), 8.90 (1H, d), 8.67-8.64 (1H, m), 7.92-7.89 (1H, m), 7.54-7.50 (1H,m), 3.01 (2H, q), 1.48 (3H, t). M3-51 ¹H-NMR (CDCl₃) δ: 10.45 (1H, s),9.57 (1H, s), 8.36 (1H, dd), 7.75 (1H, dd), 7.52 (1H, d), 7.45 (1H, dd),7.40-7.36 (1H, m), 7.11 (1H, d), 2.96 (2H, q), 1.44 (3H, t). M3-52¹H-NMR (CDCl₃), δ: 10.34 (1H, s), 8.84 (1H, s), 8.58 (1H, d), 7.92 (1H,d), 7.67 (1H, d), 7.40 (1H, dd), 7.12 (1H, d), 3.00 (2H, q), 1.47 (3H,t). M3-53 ¹H-NMR (CDCl₃) δ: 9.78 (1H, s), 8.38 (1H, d), 8.33 (1H, dd),7.96 (1H, d), 7.74 (1H, dd), 7.47-7.43 (2H, m), 5.66 (1H, s), 4.81 (2H,d), 2.95 (2H, q), 1.43 (3H, t). M3-54 ¹H-NMR (CDCl₃) δ: 9.65 (1H, s),8.56 (1H, s), 8.41 (1H, s), 7.95 (1H, d), 7.91 (1H, s), 7.47 (1H, s),5.54 (1H, t), 4.81 (2H, d), 2.99 (2H, q), 1.46 (3H, t). M3-55 ¹H-NMR(CDCl₃) δ: 9.88 (1H, s), 8.33 (1H, dd), 7.99 (1H, s), 7.74 (1H, dd),7.62 (1H, s), 7.44 (1H, dd), 4.71 (2H, s), 2.95 (2H, q), 1.43 (3H, t).M3-56 ¹H-NMR (CDCl₃) δ: 9.94 (1H, s), 8.35 (1H, dd), 8.14 (1H, d), 7.75(1H, dd), 7.60 (1H, d), 7.45 (1H, dd), 4.63 (1H, d), 3.24 (3H, d), 2.96(2H, q), 1.44 (3H, t).

TABLE 71 Intermediate compound Material value M6-1 1H-NMR (CDCl3) δ:8.76 (1H, d), 8.71 (1H, dd), 8.39 (1H, d), 7.97 (1H, dd), 7.48 (1H, dd),3.97 (3H, s). M6-17 ¹H-NMR (CDCl₃) δ: 8.97-8.95 (1H, m), 8.74-8.72 (1H,m), 8.41-8.39 (1H, m), 8.23-8.21 (1H, m), 4.03 (3H, s) M6-44 1H-NMR(CDCl3) δ: 8.65 (1H, dd), 8.09 (1H, s), 7.91 (1H, dd), 7.40 (1H, dd),6.94 (1H, s), 3.98 (3H, s), 3.81 (3H, s). M6-45 1H-NMR (CDCl3) δ: 8.69(1H, d), 8.21 (1H, s), 7.94 (1H, d), 7.65 (1H, d), 7.53-7.41 (2H, m),3.85 (3H, s). M6-46 1H-NMR (CDCl3) δ: 8.65 (1H, dd), 8.47 (1H, s), 8.08(1H, d), 7.93 (1H, dd), 7.68 (1H, d), 7.38 (1H, dd). M2-1 1H-NMR (CDCl3)δ: 8.31 (1H, d), 7.75 (1H, d), 7.49 (1H, dd), 2.97 (2H, q), 1.44 (3H,t). M2-4 1H-NMR (CDCl3) δ: 8.55 (1H, s), 7.92 (1H, s), 3.02 (2H, q),1.47 (3H, t). M18-1 1H-NMR (CDCl3) δ: 8.56 (1H, d), 7.74 (1H, d), 7.47(1H, dd), 2.99 (2H, q), 1.42 (3H, t). M20-44 1H-NMR (CDCl3) δ: 9.53 (1H,brs), 8.54 (1H, d), 7.90 (1H, d), 7.70-7.46 (3H, m), 6.76 (1H, d), 4.48(1H, brs), 2.91 (3H, d). M37-1 1H-NMR (CDCl3) δ: 8.49 (1H, dd), 7.75(1H, dd), 7.43 (1H, dd), 3.06 (2H, q), 1.38 (3H, t). M37-4 1H-NMR(CDCl3) δ: 8.68 (1H, s), 7.88 (1H, s), 3.13 (2H, q), 1.44 (3H, t).

Next, Formulation Examples will be described. Herein, the term “part(s)”means “part(s) by weight”.

Formulation Example 1

Any one of the present compounds 1 to 555 (10 parts) is dissolved in amixture of xylene (35 parts) and N,N-dimethylformamide (35 parts), andto the mixture is added polyoxyethylene styryl phenyl ether (14 parts)and calcium dodecylbenzenesulfonate (6 parts), and stirred to give anemulsifiable concentrate of each compound.

Formulation Example 2

Sodium lauryl sulfate (4 parts), calcium lignin sulfonate (2 parts), afine powder (20 parts) of synthetic hydrated silicone oxide anddiatomite (54 parts) are mixed, then to the mixture is added any one ofthe present compounds 1 to 555 (20 parts), and mixed to give a wettablepowder of each compound.

Formulation Example 3

To any one of the present compounds 1 to 555 (2 parts) is added a finepowder (1 part) of synthetic hydrated silicone oxide, calcium ligninsulfonate (2 parts), bentonite (30 parts), and kaolin clay (65 parts),and mixed. Then, to the mixture is added an appropriate amount of water,further stirred, granulated with a granulator, and draft-dried to givegranules of each compound.

Formulation Example 4

Any one of the present compounds 1 to 555 (1 part) is dissolved in anappropriate amount of acetone. To the mixture is added a fine powder (5parts) of synthetic hydrated silicone oxide, PAP (0.3 parts), andFubasami clay (93.7 parts), and well stirred. Then, acetone is removedby evaporation to give dusts of each compound.

Formulation Example 5

A mixture (weight ratio=1:1) of polyoxyethylene alkyl ether sulfateammonium salt and white carbon (35 parts), any one of the presentcompounds 1 to 555 (10 parts), and water (55 parts) are mixed,pulverized by a wet grinding method to give a suspension concentrate ofeach compound.

Formulation Example 6

Any one of the present compounds 1 to 555 (0.1 parts) is dissolved inxylene (5 parts) and trichloroethane (5 parts), and mixed withdeodorized kerosine (89.9 parts) to give an oil solutions of eachcompound.

Formulation Example 7

Any one of the present compounds 1 to 555 (10 mg) is dissolved inacetone (0.5 ml). The mixture is added to animal powdered solid feed(powdered solid feed for breeding, CE-2, from CLEA Japan, Inc.) (5 g)and mixed uniformly. Then, acetone is removed by evaporation to give apoison bait of each compound.

Formulation Example 8

Any one of the present compounds 1 to 555 (0.1 parts) and Neothiosol(Chuo Kasei Co. Ltd.) (49.9 parts) are charged into an aerosolcontainer. After an aerosol valve is attached to the container, dimethylether (25 parts) and LPG (25 parts) are charged into the container. Thecontainer is vibrated, and attaching an actuator to give an oily aerosolof each compound.

Formulation Example 9

Any one of the present compounds 1 to 555 (0.6 parts), BHT(2,6-di-tert-butyl-4-methylphenol) (0.01 parts), xylene (5 parts),deodorized kerosine (3.39 parts), and an emulsifier (Atmos 300,registered trade name for Atmos Chemical Ltd.) (1 part) are mixed anddissolved. The mixture and distilled water (50 parts) are charged intoan aerosol container, and attaching a valve. Then, propellant (LPG) (40parts) is pressure-charged into the container through the valve to givean aqueous aerosol of each compound.

Formulation Example 10

Any one of the present compounds 1 to 555 (0.1 g) is dissolved inpropylene glycol (2 ml), and the solution is impregnated into a porousceramic plate (4.0×4.0 cm, 1.2 cm thick) to give a heat-type smokingagent.

Formulation Example 11

Any one of the present compounds 1 to 555 (5 parts) and ethylene-methylmethacrylate copolymer (proportion of methyl methacrylate in thecopolymer: 10 wt %, Acryft WD301, manufactured by Sumitomo Chemical Co.,Ltd) (95 parts) are melt-mixed by a sealed, pressurized kneader(manufactured by Moriyama Co., Ltd.). The resulting mixture is extrudedfrom a molding machine via a molding die to give a rod-shaped moldedarticle (15 cm long, 3 mm diameter).

Formulation Example 12

Any one of the present compounds 1 to 555 (5 parts) and soft vinylchloride resin (95 parts) are melt-mixed by a sealed, pressurizedkneader (manufactured by Moriyama Co., Ltd.). The resulting mixture isextruded from a molding machine via a molding die to give a rod-shapedmolded article (15 cm long, 3 mm diameter).

Formulation Example 13

Any one of the present compounds 1 to 555 (100 mg), lactose (68.75 mg),corn starch (237.5 mg), microcrystalline cellulose (43.75 mg), polyvinylpyrrolidone (18.75 mg), sodium carboxymethyl starch (28.75 mg), andmagnesium stearate (2.5 mg) are mixed, and the resulting mixture iscompressed to a suitable size to give tablets.

Formulation Example 14

Any one of the present compounds 1 to 555 (25 mg), lactose (60 mg), cornstarch (25 mg), carmellose calcium (6 mg), and 5% hydroxypropylmethylcellulose (appropriate amount) are mixed, and the resulting mixture ispacked into hard shell gelatin capsules or hydroxypropyl methylcellulosecapsules to give capsules.

Formulation Example 15

To a mixture of any one of the present compounds 1 to 555 (1000 mg),fumaric acid (500 mg), sodium chloride (2000 mg), methylparaben (150mg), propylparaben (50 mg), granulated sugar (25000 mg), 70% solution ofsorbitol (13000 mg), VeegumK (VanderbiltCo) (100 mg), a perfume (35 mg),and a colorant (500 mg) is added distillated water such that the finalvolume becomes 100 ml, and well mixed to give a suspension for oraladministration.

Formulation Example 16

Any one of the present compounds 1 to 555 (5% by weight) is dissolved inPolysorbate 85 (5% by weight), benzyl alcohol (3% by weight), andpropylene glycol (30% by weight), and a phosphate buffer is addedthereto such that the pH becomes 6.0-6.5, and water is added thereto tobe a final volume to give a liquid for oral administration.

Formulation Example 17

Aluminum distearate (5% by weight) is dispersed into a fractionatedcoconut oil (57% by weight) and Polysorbate 85 (3% by weight) byheating. After cooling to room temperature, saccharine (25% by weight)is dispersed into the oily vehicle. Then, the present compounds 1 to 555(10% by weight) is added to the mixture to give a paste for oraladministration.

Formulation Example 18

Any one of the present compounds 1′ to 555 (5% by weight) and alimestone powder (95% by weight) are mixed, and then the mixture issubjected to a wet granulation method to give granules for oraladministration.

Formulation Example 19

Any one of the present compounds 1 to 555 (5 parts) is dissolved indiethylene glycol monoethyl ether (80 parts), and then propylenecarbonate (15 parts) is mixed therewith to give a spot-on liquid.

Formulation Example 20

Any one of the present compounds 1 to 555 (10 parts) is dissolved indiethylene glycol monoethyl ether (70 parts), and then 2-octyldodecanol(20 parts) is mixed therewith to give a pour-on liquid.

Formulation Example 21

To any one of the present compounds 1 to 555 (0.5 parts) are addedNikkol TEALS-42 (Nikko Chemicals Co., Ltd., 42% aqueous solution oftriethanolamine lauryl sulfate) (60 parts) and propylene glycol (20parts). After stirring and mixing enough to form a homogeneous solution,water (19.5 parts) is added thereto and the mixture is stirred and mixedadequately to give a homogeneous shampoo formulation.

Formulation Example 22

Any one of the present compounds 1 to 555 (0.15% by weight), an animalfeed (95% by weight), and a mixture (4.85% by weight) of dicalciumphosphate, diatomite, Aerosil, and carbonate (or chalk) are stirred andmixed adequately to give a premix for animal feed.

Formulation Example 23

Any one of the present compounds 1 to 555 (7.2 g) and Vosco S-55(manufactured by Maruishi Pharmaceutical Co., Ltd.) (92.8 g) aredissolved and mixed at 100° C. Then, the mixture is poured into asuppository mold, and cooled and solidified to give a suppository.

The controlling effect on pests by the present compound will bedemonstrated below with reference to Test Examples.

Test Example 1

Each test solution was prepared by diluting a formulation containing anyof the present compounds 1-9, 12-16, 18-20, 22-28, 30-32, 36-37, 40, 44,46-48, 50-51, 56, 60, 62-65, 69-70, 72, 74, 76, 79-81, 84-85, 89, 99,138, 144, 190, 508, 511-515, 517-524, 526 and 528-529 as obtained inFormulation Example 5, with water so as to give 500 ppm of theconcentration of the active ingredient.

On the other hand, on a cucumber seedling (the first true leaf stage)planted in a plastic cup was inoculated with about 30 Aphis gossypii(whole stage), and leaving it for a day. Twenty (20) ml of each testsolution was sprayed on the seedling.

Six (6) days after spraying, the number of the surviving Aphis gossypiiparasitized on the leaves of the cucumber was examined, and a controlvalue was calculated according to the following equation:

Controlling value (%)={1−(Cb×Tai)/(Cai×Tb)}×100

wherein the symbols represent as follows:

Cb: the number of insects in a non-treated section before treatment

Cai: the number of insects in a non-treated section on observation

Tb: the number of insects in a treated-section before treatment

Tai: the number of insects in a treated section on observation

wherein the non-treated section represents a section where the testdiluted solution prepared by diluting the formulation without thepresent compound as in Formulation Example 5 with the same amount ofwater as in the treated-section was used.

As a result, in the treated-section using each test solution containingeach of the present compounds 1-9, 12-16, 18-20, 22-28, 30-32, 36-37,40, 44, 46-48, 50-51, 56, 60, 62-65, 69-70, 72, 74, 76, 79-81, 84-85,89, 99, 138, 144, 190, 508, 511-515, 517-524, 526 and 528-529, thecontrol value was 90% or more.

Test Example 2

Each test solution was prepared by diluting a formulation containing anyof the present compounds 1-3, 5-8, 13-16, 19-20, 25, 27, 30, 32, 36-37,44, 47-48, 50-51, 60, 62-64, 72, 81, 85, 99, 138, 144, 511-512, 515,518, 522-524 and 528 as obtained in Formulation Example 5, with water soas to give 500 ppm of the concentration of the active ingredient.

On the other hand, a cucumber seedling (the second true leaf stage)planted in a plastic cup was drenched at its foot with 5 ml of each ofthe diluted solutions, and kept in a greenhouse of 25° C. for 7 days. Onthe cucumber leaf surface was inoculated with about 30 Aphis gossypii(whole stage), and further kept in the greenhouse for 6 days, then thenumber of insect of living Aphis gossypii parasitized on the leaves ofthe cucumber was examined, and a control value was calculated accordingto the following equation:

Controlling value (%)={1−(Cb×Tai)/(Cai×Tb)}×100

wherein the symbols represent as follows:

Cb: the number of insects in a non-treated section before treatment

Cai: the number of insects in a non-treated section on observation

Tb: the number of insects in a treated-section before treatment

Tai: the number of insects in a treated section on observation

wherein the non-treated section represents a section where the testdiluted solution prepared by diluting the formulation without thepresent compound as in Formulation Example 5 with the same amount ofwater as in the treated-section was used.

As a result, in the treated-section using each test solution containingeach of the present compounds 1-3, 5-8, 13-16, 19-20, 25, 27, 30, 32,36-37, 44, 47-48, 50-51, 60, 62-64, 72, 81, 85, 99, 138, 144, 511-512,515, 518, 522-524 and 528, the control value was 90% or more.

Test Example 3

Each test solution was prepared by diluting a formulation containing anyof the present compounds 1-3, 5-9, 12-20, 22, 24-30, 32, 36-37, 44, 50,60, 62-64, 72, 74, 81, 84-85, 89, 99, 138, 144, 511, 515, 518-519, 521,523-524 and 529 as obtained in Formulation Example 5, with water so asto give 500 ppm of the concentration of the active ingredient.

On the other hand, a rice seedling (the second leaf stage) planted in apolyethylene cup was sprayed with 10 ml of each test solution. Afterair-drying, 20 third-fourth instar larvae of Nilaparvata lugens werereleased, and kept in the greenhouse of 25° C. After 6 days, the numberof insect of living Nilaparvata lugens parasitized on the rice wasexamined, and a control value was calculated according to the followingequation:

Controlling value (%)={1−(Cb×Tai)/(Cai×Tb)}×100

wherein the symbols represent as follows:

Cb: the number of insects in a non-treated section before treatment

Cai: the number of insects in a non-treated section on observation

Tb: the number of insects in a treated-section before treatment

Tai: the number of insects in a treated section on observation

wherein the non-treated section represents a section where the testdiluted solution prepared by diluting the formulation without thepresent compound as in Formulation Example 5 with the same amount ofwater as in the treated-section was used.

As a result, in the treated-section using each test solution containingeach of the present compounds 1-3, 5-9, 12-20, 22, 24-30, 32, 36-37, 44,50, 60, 62-64, 72, 74, 81, 84-85, 89, 99, 138, 144, 511, 515, 518-519,521, 523-524 and 529, the control value was 90% or more.

Test Example 4

Each test solution was prepared by diluting a formulation containing anyof the present compounds 1-3, 5-6, 8, 12-16, 18-19, 22, 24-27, 29, 32,36-37, 44, 48, 50, 60, 62-64, 72, 74, 81, 85, 89, 99, 138, 144, 508,512, 515, 518-519 and 521-524 as obtained in Formulation Example 5, withwater so as to give 500 ppm of the concentration of the activeingredient.

On the other hand, a rice seedling (2 weeks after sowing, the secondleaf stage) planted in a plastic cup was drenched at its foot with 5 mlof each test solution, and kept in a greenhouse of 25° C. for 7 days.Twenty (20) third-fourth instar larvae of Nilaparvata lugens werereleased, and further kept in the greenhouse for 6 days, then the numberof insect of living Nilaparvata lugens parasitized on the rice wasexamined, and a control value was calculated according to the followingequation:

Controlling value (%)={1−(Cb×Tai)/(Cai×Tb)}×100

wherein the symbols represent as follows:

Cb: the number of insects in a non-treated section before treatment

Cai: the number of insects in a non-treated section on observation

Tb: the number of insects in a treated-section before treatment

Tai: the number of insects in a treated section on observation

wherein the non-treated section represents a section where the testdiluted solution prepared by diluting the formulation without thepresent compound as in Formulation Example 5 with the same amount ofwater as in the treated-section was used.

As a result, in the treated-section using each test solution containingeach of the present compounds 1-3, 5-6, 8, 12-16, 18-19, 22, 24-27, 29,32, 36-37, 44, 48, 50, 60, 62-64, 72, 74, 81, 85, 89, 99, 138, 144, 508,512, 515, 518-519 and 521-524, the control value was 90% or more.

Test Example 5

Each test solution was prepared by diluting a formulation containing anyof the present compounds 3, 5-6, 8, 13-16, 18-20, 24-27, 29, 36-37, 44,47, 60, 63-64, 72, 74, 89, 99, 511, 515, 518, 521, 523-524 and 528 asobtained in Formulation Example 5, with water so as to give 500 ppm ofthe concentration of the active ingredient.

On the other hand, Bemisia tabaci adult was released on a tomatoseedling (the third true leaf stage) planted in a polyethylene cup, andmade to lay eggs for about 72 hours. The tomato seedling was kept in agreenhouse for 8 days. When instar larvae hatched from the eggs, theabove test spray solution was sprayed in the amount of 20 ml/cup. Thecup was kept in a greenhouse at 25° C. After the keeping for 7 days, thenumber of surviving instar larvae on the tomato leaves was examined, anda control value was calculated according to the following equation:

Controlling value (%)={1−(Cb×Tai)/(Cai×Tb)}×100

wherein the symbols represent as follows:

Cb: the number of insects in a non-treated section before treatment

Cai: the number of insects in a non-treated section on observation

Tb: the number of insects in a treated-section before treatment

Tai: the number of insects in a treated section on observation

wherein the non-treated section represents a section where the testdiluted solution prepared by diluting the formulation without thepresent compound as in Formulation Example 5 with the same amount ofwater as in the treated-section was used.

As a result, in the treated-section using each test solution containingeach of the present compounds 3, 5-6, 8, 13-16, 18-20, 24-27, 29, 36-37,44, 47, 60, 63-64, 72, 74, 89, 99, 511, 515, 518, 521, 523-524 and 528,the control value was 90% or more.

Test Example 6

Each test solution was prepared by diluting a formulation containing anyof the present compounds 1-5, 8-9, 11-12, 15-16, 19-20, 22-25, 27-33,35-37, 40, 44, 46-51, 53, 58-65, 69, 71-74, 76-78, 80-85, 87, 89, 99,138, 144, 190, 505-506, 508, 511-515, 518, 520-523 and 527-530 asobtained in Formulation Example 5, with water so as to give 500 ppm ofthe concentration of the active ingredient.

On the other hand, Cabbage (the third leaf stage) planted in apolyethylene cup was sprayed with 20 mL/cup of each test solution. Afterthe test solution was dried, the aerial part was cut off, and thenplaced in a 50 mL volume cup. Five (5) second instar larvae of Plutellaxylostella were released into the cup, and the cup was sealed with alid. After the cup was kept at 25° C. for 5 days, the number of livinginsects was counted. A death rate was calculated according to thefollowing equation:

Death rate (%)=(Number of dead insects/Number of tested insects)×100

As a result, in the treated-section using each test solution containingeach of the present compounds 1-5, 8-9, 11-12, 15-16, 19-20, 22-25,27-33, 35-37, 40, 44, 46-51, 53, 58-65, 69, 71-74, 76-78, 80-85, 87, 89,99, 138, 144, 190, 505-506, 508, 511-515, 518, 520-523 and 527-530, thedeath rate was 80% or more.

Test Example 7

Each test solution was prepared by diluting a formulation containing anyof the present compounds 1-9, 11-20, 22-35, 38-40, 44, 46-48, 50, 53,58, 60, 62-64, 71-72, 74, 77-85, 87, 89, 99, 138, 144, 505-506, 508,511-512, 514-515, 518-520, 523-526 and 528-530 as obtained inFormulation Example 5, with water so as to give 500 ppm of theconcentration of the active ingredient.

On the other hand, an apple tree was planted in a plastic cup, and grownuntil the seventh-eighth leaf was spread. The apple tree was sprayedwith 20 mL/cup of each test solution. After the test solution was dried,60 first-instar Adoxophyes orana fasciata were released, and the cup wascovered with a plastic cup upside-down which the bottom was cut off anda filter paper was put thereon. After 7 days, the number of livinginsects was counted, and a death rate was calculated according to thefollowing equation:

Death rate (%)=(Number of dead insects/Number of tested insects)×100

As a result, in the treated-section using each test solution containingeach of the present compounds 1-9, 11-20, 22-35, 38-40, 44, 46-48, 50,53, 58, 60, 62-64, 71-72, 74, 77-85, 87, 89, 99, 138, 144, 505-506, 508,511-512, 514-515, 518-520, 523-526 and 528-530, the death rate was 90%or more.

Test Example 8

Each test solution was prepared by diluting a formulation containing anyof the present compounds 1, 3-5, 8, 15-16, 19-20, 23, 27, 29, 37, 40,44, 48, 60-61, 64, 72, 74, 518, 523 and 528 as obtained in FormulationExample 5, with water so as to give 500 ppm of the concentration of theactive ingredient.

A filter paper having a diameter of 5.5 cm was spread on the bottom of apolyethylene cup having a diameter of 5.5 cm and each test solution (0.7ml) was added dropwise onto the filter paper. As a bait sucrose (30 mg)was uniformly placed on the filter paper. Into the polyethylene cup, 10female imagoes of Musca domestica were released and the cup was sealedwith a lid. After 24 hours, the number of surviving Musca domestica wasexamined and the death rate of the pest was calculated.

As a result, in the treatment with each test solution containing each ofthe present compounds 1, 3-5, 8, 15-16, 19-20, 23, 27, 29, 37, 40, 44,48, 60-61, 64, 72, 74, 518, 523 and 528, the death rate was 100%.

Test Example 9

Each test solution was prepared by diluting a formulation containing anyof the present compounds 4-5, 19-20, 28-29, 40, 44, 48, 60, 71-74, 89,523 and 528 as obtained in Formulation Example 5, with water so as togive 500 ppm of the concentration of the active ingredient.

A filter paper having a diameter of 5.5 cm was spread on the bottom of apolyethylene cup having a diameter of 5.5 cm and each test solution (0.7ml) was added dropwise onto the filter paper. As a bait sucrose (30 mg)was uniformly placed on the filter paper. Into the polyethylene cup, 2male imagoes of Blattalla germanica were released and the cup was sealedwith a lid. After 6 days, the number of surviving Blattalla germanicawas examined and the death rate of the pest was calculated.

As a result, in the treatment with each test solution containing each ofthe present compounds 4-5, 19-20, 28-29, 40, 44, 48, 60, 71-74, 89, 523and 528, the death rate was 100%.

Test Example 10

Each test solution was prepared by diluting a formulation containing anyof the present compounds 1, 3-5, 8, 15-16, 19-20, 22-25, 27-28, 31-33,35, 37, 40, 44, 48-49, 51, 59-64, 71-74, 80-81, 84-85, 89, 99, 138, 144,505-506, 508, 514-515, 518, 520, 522-523 and 528 as obtained inFormulation Example 5, with water so as to give 500 ppm of theconcentration of the active ingredient.

To ion-exchanged water (100 mL), each test solution (0.7 ml) was added(active ingredient concentration: 3.5 ppm). Into the solution, 20last-instar larvae of Culex pipiens pallens were released. One dayafter, the number of surviving Culex pipiens pallens was examined andthe death rate of the pest was calculated.

As a result, in the treatment with each test solution containing each ofthe present compounds 1, 3-5, 8, 15-16, 19-20, 22-25, 27-28, 31-33, 35,37, 40, 44, 48-49, 51, 59-64, 71-74, 80-81, 84-85, 89, 99, 138, 144,505-506, 508, 514-515, 518, 520, 522-523 and 528, the death rate was 95%or more.

Test Example 11

Each 2 mg of the present compounds 1, 5, 8, 15-16, 19, 23, 25-27, 30,37, 40, 49, 61, 63, 99 and 516 was put into a screw tube (Maruemu No. 5;27×55 mm). Acetone (0.2 ml) was added thereto and sealed with a cap.After dissolving the compound in acetone, the screw tube was rotated andinverted to uniformity coat the solution onto the whole inner wall ofthe tube. After removing the cap, the solution was air-dried for about 2hours. Then, non-blood-sucking nymphal ticks, Haemaphysalis longicornis(5 ticks/group) were released into the tube, and the tube was sealedwith the cap. After 2 days, the number of dead tick was counted, and adeath rate was calculated according to the following equation:

Death rate (%)=(Number of dead tick/Number of tested tick)×100

As a result, in the treatment with each test solution containing each ofthe present compounds 1, 5, 8, 15-16, 19, 23, 25-27, 30, 37, 40, 49, 61,63, 99 and 516, the death rate was 100%.

INDUSTRIAL APPLICABILITY

The present compound has a controlling effect on pests and is useful asan active ingredient of a pest control agent.

1.-21. (canceled)
 22. A compound represented by the formula (M6-1):

wherein V² represents a halogen atom, A^(1a) represents —NR^(7a)—, anoxygen atom or a sulfur atom, A^(3a) represents a nitrogen atom or═CR^(9a)—, R^(2a) and R^(4a) are the same or different and eachrepresents a halogen atom or a hydrogen atom, R^(3a) represents a C1-C6alkyl group optionally substituted by one or more halogen atoms, a C2-C6alkenyl group optionally substituted by one or more halogen atoms, aC2-C6 alkynyl group optionally substituted by one or more halogen atoms,5- or 6-membered aromatic heterocyclic group (wherein the 5- or6-membered aromatic heterocyclic group is optionally substituted by oneor more atoms or groups selected from the group consisting of a halogenatom, a C1-C3 alkyl group optionally substituted by one or more halogenatoms, and a C1-C3 alkoxy group optionally substituted by one or morehalogen atoms), —OR^(20a) (wherein R^(20a) represents a C1-C6 alkylgroup optionally substituted by one or more halogen atoms),—S(O)_(m)R^(21a) (wherein R^(21a) represents a C1-C6 alkyl groupoptionally substituted by one or more halogen atoms, m represents 0, 1or 2), a cyano group, a nitro group, a halogen atom or a hydrogen atom,R^(5a) represents a C1-C6 alkyl group optionally substituted by one ormore halogen atoms, —OR^(22a) (wherein R^(22a) represents a C1-C6 alkylgroup optionally substituted by one or more halogen atoms),—S(O)_(m)R^(23a) (wherein R^(23a) represents a C1-C6 alkyl groupoptionally substituted by one or more halogen atoms, m represents 0, 1or 2), —SF₅ or a halogen atom, R^(7a) represents a C1-C6 alkyl groupoptionally substituted by one or more halogen atoms, a C3-C6 alkenylgroup optionally substituted by one or more halogen atoms, a C3-C6alkynyl group optionally substituted by one or more halogen atoms, or aC1-C6 alkyl group substituted by one 5- or 6-membered aromaticheterocyclic group, (wherein the 5- or 6-membered aromatic heterocyclicgroup is optionally substituted by one or more atoms or groups selectedfrom the group consisting of a halogen atom, a C1-C3 alkyl groupoptionally substituted by one or more halogen atoms, and a C1-C3 alkoxygroup optionally substituted by one or more halogen atoms), and R^(9a)represents a C1-C6 alkyl group optionally substituted by one or morehalogen atoms, —OR^(24a) (wherein R^(24a) represents a C1-C6 alkyl groupoptionally substituted by one or more halogen atoms), —S(O)_(m)R^(25a)(wherein R^(25a) represents a C1-C6 alkyl group optionally substitutedby one or more halogen atoms, m represents 0, 1 or 2), a halogen atom ora hydrogen atom, or an N-oxide thereof. 23-25. (canceled)
 26. Thecompound according to claim 22, wherein A^(1a) is —NR^(7a)— in theformula (M6-1).